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Questions we hear every week, answered properly.
Thirty-six plain-English answers from our CPAs and Enrolled Agents — on getting started, fees, security, real estate, IRS letters and running a small business. Search, or browse by topic below.
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Every answer below is written by the person who does that work. If your situation is more specific, book a free discovery call — that's what it's for.
Getting started
Less than you'd think. For the first conversation we want:
- Your last two years of returns (federal and state)
- Photo ID and Social Security numbers for everyone on the return
- This year's income documents as they arrive — W-2s, 1099s, K-1s, brokerage statements
- Business owners: a year-end profit & loss and balance sheet, or read-only access to your books
- Landlords and investors: closing statements, rent rolls and a summary of expenses by property
Upload everything to the secure portal before we meet and the first hour is spent on planning, not paperwork. Our document checklist lists every form by situation.
Everything can be done remotely, and for most clients it is. Since 2020 every engagement runs through an encrypted client portal with e-signature and video planning sessions — we currently serve clients in 14 states, and the planning conversation is exactly the same over video as across the table.
If you'd rather meet in person, you're welcome at 210 Harbor Drive, Suite 400, downtown San Diego. Many clients come in once for onboarding and go virtual from there. Book either kind of meeting here.
Most individual returns are finished 7–10 business days after we have complete documents; business, trust and multi-entity returns take two to three weeks. Every return is reviewed by a second credentialed professional before it reaches you, and that review is never skipped to hit a date.
Documents that arrive in the last two weeks before a deadline are usually placed on extension so they get the same care — see the next question for why that costs you nothing.
- March 15 — S-corporation and partnership returns (Forms 1120-S and 1065)
- April 15 — individual (1040) and C-corporation returns, plus the first quarterly estimate
- June 15, September 15, January 15 — remaining quarterly estimates
- October 15 — extended individual deadline (September 15 for extended business returns)
An extension gives you six more months to file, not to pay. So we calculate what you'll owe, pay it with the extension, and there's no penalty and no interest. Extensions are free for clients and often produce a better return than a rushed April one. Full dates are on our deadline calendar.
A named CPA or Enrolled Agent from our team page prepares and signs your return. A second credentialed reviewer checks it line by line. Daniel Brooks' client-success team handles scheduling, documents and reminders, so your advisor's time goes to your plan.
You meet your advisor during onboarding and keep the same person year after year — no seasonal staff, no rotating call center.
Yes — 30 minutes, no card, no obligation. Bring last year's return and whatever's on your mind. You'll leave with two or three specific, dollar-ranked ideas whether or not you hire us, and if we're not the right fit we'll say so and point you somewhere better. Pick a time.
Pricing & billing
Fixed fees, published in full on our pricing page:
- Essentials — from $249 per individual return (federal + one state)
- Growth — from $149/month for small businesses: monthly books, payroll coordination and business + personal returns
- Portfolio — from $399/month for real-estate investors with up to three entities
- Enterprise — custom quotes for trusts, estates and multi-state groups
Every fee is quoted in writing before work begins, and it doesn't change unless the scope does. There is no hourly meter and no charge for a quick question.
Complexity, not time. The common add-ons are additional state returns, many K-1s or rental properties, foreign accounts and FBAR filings, cryptocurrency activity, equity compensation (RSUs, ISOs, ESPP) and multi-entity structures. Each is a published line item, quoted after your intake questionnaire — you'll always see the full number before we start, never on the invoice.
It depends on why. If an amendment is needed because of our error, it's free — and we cover any penalties and interest that result. If it's driven by new information (a late K-1, a corrected 1099) or corrects a return prepared elsewhere, amended returns start at $275 and are quoted up front. Either way, we'll tell you first whether amending is actually worth it.
Growth and Portfolio packages are billed monthly by card or ACH and can be canceled with 30 days' notice. Essentials returns can be split into two payments — half at engagement, half at delivery. We never hold a finished return hostage for payment.
No. Quarterly planning check-ins are included in every package — they're the point of the firm, not an upsell. Larger one-off projects such as restructuring entities, coordinating a cost-segregation study or modeling a business sale are scoped and quoted separately as fixed-fee projects, so you can decide with the number in front of you. More on year-round planning.
No. Our fee never depends on the size of your refund or the tax we save you. Contingent fees on original returns are prohibited for practitioners under IRS Circular 230, and a fee tied to the refund creates exactly the wrong incentive. You pay for the work; the savings are yours.
Documents & security
You receive an email invitation, set a password and turn on multi-factor authentication (required, not optional). From there you can:
- Upload documents from a computer, or photograph them with the mobile app
- Sign engagement letters and Form 8879 electronically
- Message your advisor — replies are answered within one business day
- Download every return and plan we've prepared for you, any time
Data is encrypted in transit and at rest, access is logged, and your documents are retained in the vault for seven years.
Please don't. Ordinary email isn't encrypted end to end, and a single W-2 contains everything an identity thief needs to file a fraudulent return in your name. Use the portal upload or the mobile camera capture — it takes the same thirty seconds. If something arrives by email anyway, we move it into the portal and permanently delete the message.
We use it only to provide the services you've engaged us for. We never sell it, never share it with marketers, and any use beyond preparing your return requires your written consent under IRS §7216. We maintain the written information security plan (WISP) the IRS requires of every tax professional, train staff annually, and securely destroy records once the retention period ends.
After you review the draft with your advisor, you sign IRS Form 8879 (the e-file authorization) electronically in the portal, with a short identity-verification step. On a joint return both spouses sign separately. We then e-file and post the IRS and state acceptance confirmations to your portal — usually within 24 hours.
Every return we prepare stays in your portal vault for at least seven years, so a lender or immigration request is a two-click download rather than a phone call. For years before you joined us, we can request IRS wage, income and account transcripts on your behalf with Form 8821 — no need to dig through old files.
The IRS issues most e-filed refunds with direct deposit within 21 days of acceptance. Two exceptions: returns claiming the Earned Income Credit or Additional Child Tax Credit are held until mid-February by law, and paper checks take several weeks longer than direct deposit. California refunds typically arrive in two to three weeks. We show you how to track both with the IRS "Where's My Refund?" tool and the FTB's equivalent — and if a refund is late, we chase it.
Real estate
Five things, in order:
- Investment property both sides — the property sold and the one bought must be held for investment or business use (your home doesn't qualify)
- A qualified intermediary before closing — you can never touch the sale proceeds, even for a day
- 45 days to identify replacement property in writing, from the day you close the sale
- 180 days to close on the replacement (or your return due date, if sooner — we extend it)
- Equal or greater value and debt, with all equity reinvested, to defer the full gain
Before you list, we model whether the exchange actually beats paying the tax — sometimes it doesn't. See the Acquire / Operate / Exit framework.
Usually yes when three things line up: a depreciable basis above roughly $500,000, a hold of several years, and income the accelerated depreciation can actually offset — typically real estate professional status, a short-term rental you materially participate in, or other passive income. Recapture at sale is real, so the value is in timing, not free money. We model the study fee, the first-year deduction and the exit before you commission anything.
That's a liability question first, so we coordinate with your attorney. On the tax side: a single-member LLC is disregarded and changes nothing on your return; a multi-member LLC files a partnership return (Form 1065, due March 15). In California every LLC owes at least the $800 annual franchise tax, and your lender may need to consent to a title transfer. We map the cost against the protection — and the alternatives, such as umbrella insurance — before you form anything.
REPS lets rental losses offset wages and business income instead of being suspended as passive. To qualify you (or your spouse) must spend more than 750 hours a year, and more than half of your total working time, in real property trades you materially participate in — and separately materially participate in your rentals, usually with an election to treat them as one activity. Full-time W-2 employees almost never qualify. It requires contemporaneous time logs; we set up the tracking so it holds up in an audit.
Repairs that keep the property in ordinary operating condition (patching a roof, replacing a faucet) are deducted in the year paid. Improvements that better, restore or adapt the property (a new roof, a kitchen remodel) are capitalized and depreciated. Three IRS safe harbors do most of the work: the $2,500 de minimis election per item or invoice, the routine maintenance safe harbor, and the small-taxpayer safe harbor for buildings under $1 million. We apply them invoice by invoice during monthly bookkeeping, so it's decided long before April.
Three layers. Federal long-term capital gains tax at 0%, 15% or 20% on the appreciation; the 3.8% net investment income tax if your income is high enough; and unrecaptured §1250 gain — the depreciation you took (or should have taken) — taxed at up to 25%. California taxes the entire gain as ordinary income at your regular rate. A 1031 exchange, an installment sale or opportunity-zone reinvestment can defer some or all of it, but only if it's planned before escrow opens.
IRS & notices
Don't panic, and don't put it in a drawer. Do this instead:
- Find the notice number (top right — CP2000, CP14, LTR 3172 and so on) and the response deadline, usually 30 days
- Upload the whole letter, every page, to your portal — or send it to us if you're not yet a client
- Don't call the IRS or send payment until we've read it
Many notices are automated matching errors — a 1099 reported twice, a payment applied to the wrong year. We review it within one business day and, with a signed Form 2848 power of attorney, respond to the IRS on your behalf so you never have to. IRS representation services.
Both have unlimited rights to represent you before the IRS — audits, appeals and collections. An Enrolled Agent is licensed directly by the U.S. Treasury, specifically in taxation, after a three-part exam or IRS experience. A CPA is licensed by the state in accounting more broadly, of which tax is one part. Our resolution practice is led by Marcus Chen, EA, a former IRS revenue agent, with a CPA reviewing the tax positions — you get both.
First, file on time anyway — the failure-to-file penalty (5% a month) is ten times the failure-to-pay penalty (0.5% a month). Then choose the right path:
- Short-term payment plan — up to 180 days, no setup fee
- Streamlined installment agreement — balances up to $50,000 over up to 72 months, no financial disclosure
- Offer in Compromise — settle for less when you genuinely cannot pay in full
- Currently not collectible — collection paused while you're in hardship
First-time penalty abatement often removes the penalties entirely if your prior three years were clean. We handle the request.
This is far more common than you think, and it's fixable. The IRS generally requires the last six years to be filed to be considered compliant. We pull your wage-and-income transcripts so nothing is missed, prepare the returns in order, replace any "substitute for return" the IRS filed for you (those never include your deductions), and request penalty relief. One fixed fee covers the whole catch-up, and you stop getting the letters.
Yes — correspondence, office and field audits, federal and California. Once we hold power of attorney the IRS deals with us, not you; you don't attend meetings and you don't answer questions on the spot. We assemble the documentation, respond in writing and, if needed, take the case to Appeals. Resolution work is quoted as a fixed-fee engagement, and clients whose returns we prepared receive audit support at no charge.
Meet a safe harbor (yes, that's where our name comes from). Pay in through withholding and quarterly estimates at least 100% of last year's total tax — 110% if your adjusted gross income was over $150,000 — or 90% of this year's tax, whichever is less. Do that and there's no penalty even if you owe a large balance in April. We calculate each quarterly estimate and send the payment links so the safe harbor is met every year, automatically.
Small business
It usually pays once net profit is consistently above roughly $60,000–$80,000 after a reasonable salary, because distributions above that salary avoid the 15.3% self-employment tax. The costs: running payroll for yourself, a separate return (Form 1120-S, due March 15) and California's 1.5% franchise tax with an $800 minimum. Form 2553 is due by March 15 of the year the election takes effect, and late-election relief is often available. We model your actual numbers before recommending it — the rule of thumb is a starting point, not an answer. Business tax services.
About twenty minutes. Connect your business bank and card feeds to QuickBooks or Xero once; keep business and personal spending on separate cards; answer a short monthly list of transactions we couldn't categorize; and upload receipts for larger purchases. We reconcile, review and deliver your profit & loss and balance sheet by the 5th of the following month, with a note on anything that changed your tax picture. Bookkeeping & payroll details.
Yes. We set up and review payroll through Gusto — including quarterly Form 941 and California DE 9 filings and year-end W-2s — and prepare 1099-NEC forms by January 31 for contractors paid above the reporting threshold. One habit saves a lot of January stress: collect a signed Form W-9 from every contractor before you pay them.
Federal estimates are due April 15, June 15, September 15 and January 15. California uses the same dates but front-loads the amounts — 30%, 40%, 0% and 30% of the year's total — which catches a lot of new owners in June. We compute both each quarter from your actual books and send a reminder with the IRS Direct Pay and FTB Web Pay links a week ahead. The full schedule is on our deadline calendar.
- Home office — the space must be used regularly and exclusively for business. Take the simplified rate (up to 300 sq ft) or actual costs, whichever is larger.
- Vehicle — the IRS standard mileage rate or actual expenses. Either way you need a mileage log; an app on your phone is enough.
- Meals — 50% deductible when business is discussed with a client, prospect or colleague. Entertainment (tickets, golf) is not deductible.
- The big ones people miss — retirement plan contributions, health insurance for owners, and the qualified business income deduction.
Yes — it's one of the quiet benefits of monthly bookkeeping. Lenders typically want two years of business and personal returns plus a year-to-date profit & loss and balance sheet that reconcile to your bank statements. Because your books are closed every month, those are ready the day you ask. We also prepare the CPA comfort letters and interim statements underwriters request, and we'll flag a year ahead if a planned deduction would hurt your qualifying income.
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Talk to Harbor Tax
Mon–Fri 8:30 AM – 6:00 PM · Sat 9:00 AM – 1:00 PM (Jan–Apr)
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Phone(949) 849-9825
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Email[email protected]
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Office210 Harbor Drive, Suite 400
San Diego, CA 92101
Free 30-minute discovery call
The best question is the one you ask before the deal.
Bring last year's return and whatever's coming up. You'll leave with two or three specific, dollar-ranked ideas — whether or not you hire us.