The Standing File
Most firms open your file in February and close it in April. This one never closes.
A year-round tax strategy engagement for high-income individuals and for business owners — a named advisor who knows your situation, quarterly counsel, every return and every notice handled, and someone to call before you do the thing, not after.
From a $500,000 salary to a
$126,000 tax-savings strategy.
Here is what strategic tax planning can look like. The client was earning $500,000 in W-2 income. On paper, an incredible income. Then came the taxes.
| Gross income | $500,000 |
|---|---|
| Federal income tax | ~$141,253 |
| State income tax | ~$25,000 |
| Social Security | ~$10,114 |
| Medicare | ~$9,950 |
| Estimated total taxes | ~$187,000 |
| Estimated take-home | ~$313,000 |
Nearly 37% of gross income was going to taxes before there was any chance to spend or invest it.
The question was never “how do we make less money?” It was “how do we legally keep more of what we’re already earning?”
Combine the tax planning with
an asset worth owning.
Rather than accept the bill, we looked for a move that did two jobs at once. It centred on the purchase of a $995,000 short-term rental property — but buying it was only the beginning. What mattered was how it was structured and depreciated.
Cost segregation
A cost segregation study was performed. Instead of depreciating substantially all of the building over the traditional 27.5-year residential period, the study identified qualifying components that could be depreciated over shorter recovery periods — approximately $248,352 of accelerated and bonus depreciation.
The seven-day test
Rental losses are ordinarily passive, and passive losses cannot offset wages. But the average guest stay was seven days or less, which can take the activity outside the definition of a rental activity for purposes of IRC §469.
Material participation
The client self-managed the property and participated in its operations. Where the short-term-rental and material-participation requirements are both satisfied, the losses may be treated as nonpassive — and nonpassive losses can offset W-2 income.
Generating a large deduction was only half the work. A deduction that cannot reach the income it was meant to offset is worth nothing. Combined with other eligible depreciation and deductions on the property, estimated first-year deductions reached approximately $340,676 — and the §469 analysis is what allowed them to land against a salary.
What happened to the exposure.
Gross W-2 income, exposed to federal and state income tax before other deductions.
Remaining income before other applicable adjustments, after illustrative short-term rental deductions of $340,676.
On the assumptions used in this case.
From the property itself, separately from the tax result.
And the client still owns the underlying real estate.
The asset is the part that keeps working.
Instead of writing a larger cheque to the government, the client used a legitimate planning strategy built around acquiring an income-producing asset. That asset can go on to:
- Generate cash flow
- Build equity
- Appreciate over time
- Create future tax-planning opportunities
The Standing File isn’t a folder.
It’s a proactive conversation.
Most firms wait until tax season to discover what you did last year. We meet quarterly so that entity selections, asset timing, and deduction structures are locked in before the tax year closes.
- Quarterly tax forecasting & safe harbor checks
- Real estate, equipment & retirement election modeling
- Direct access to your dedicated strategist all year
Anyone can tell you what you owe
after the year is over.
Our job is to help you understand what you can do before it is. That means looking past the return, at income, investments, business, real estate, deductions, tax exposure and long-term wealth strategy as one connected picture.
Real estate
Short-term rental strategies, cost segregation, bonus depreciation, material participation, and real estate tax planning.
Business and entity
Entity structure, owner compensation, and the retirement strategies that follow from both.
Timing
Year-end planning and multi-year projections, so a decision is priced before the transaction happens rather than after.
The objective isn’t to chase deductions. It’s to make better decisions with the tax already counted.
You earned the money.
Now let’s talk
about how much you keep.
If you are earning $250,000, $500,000, a million or more, tax preparation alone may not be enough. We help high-income professionals, executives, entrepreneurs and investors find legitimate opportunities to reduce exposure while building long-term wealth.
See the bigger picture before you file.
This case study is provided for illustrative and educational purposes. Figures are based on specific assumptions and should not be interpreted as guaranteed results. Actual tax savings depend on filing status, state of residence, income, property allocation, financing, cost-segregation results, basis, at-risk limitations, material participation, property operations, applicable tax law and other individual circumstances. Depreciation may also have future tax consequences, including depreciation recapture. Consult a qualified tax professional regarding your individual circumstances.
Three things you are actually buying.
A dedicated tax advisor
One named person, not a queue and not whoever is free. They hold your file, they know what you did last year and why, and their number is in your phone. You will not explain your situation from scratch again.
Counsel across the whole year
A quarterly session on the calendar, a written strategy plan, a mid-year projection, and a year-end review — plus unlimited questions in between. The point is to reach every decision before it hardens into a filing.
Everything filed and handled
Your returns, your estimates, your notices. Included, not billed. When an envelope arrives from the IRS or a state, you forward it and stop thinking about it — that is the service.
Built for the two situations that need it.
Same spine — named advisor, quarterly counsel, everything filed. What changes is the work underneath, because a high W-2 and equity package is a different animal from an operating business.
Large W-2 or professional income, equity compensation, investment and rental portfolios, a liquidity event on the horizon.
- Equity compensation — RSU vesting, ISO and NSO exercise timing, 83(b) decisions
- Capital gains planning, loss harvesting and holding-period management
- Alternative minimum tax exposure modelled before it lands
- Net investment income tax and the additional Medicare tax
- Charitable strategy — bunching, donor-advised funds, appreciated stock
- Backdoor and mega-backdoor Roth mechanics, done correctly
- Rental and real estate positions, including passive loss rules
- State residency and part-year planning for moves and second homes
- Annual gift exclusion use and coordination with your estate attorney
An operating company, or several. Partnerships, S-corps and C-corps, single-state or spread across the country.
- Entity structure and elections, reviewed every year rather than once
- Owner compensation, distributions and basis tracking
- Accountable plan, home office, vehicle and reimbursement policy
- Retirement plan design — Solo 401(k), SEP, SIMPLE, cash balance
- Qualified business income treatment and how to protect it
- Depreciation strategy, bonus versus §179, cost segregation coordination
- Multi-state nexus, apportionment and registration monitoring
- R&D credit qualification and study coordination
- Succession, basis and exit planning well ahead of a sale
No line items. No surprise invoices.
Everything below is inside the annual fee. The reason is simple: a client who hesitates before calling their tax advisor is a client who calls too late.
- Quarterly strategy sessions — four a year, scheduled, with an agenda and notes
- Written annual strategy plan — quantified, with an implementation calendar
- Mid-year projection — your year run forward while it can still be changed
- Year-end review — the closing window, worked properly in November
- Transaction support — call before the purchase, the sale or the exercise
- Unlimited questions — email or phone, no clock running
- Second Look on prior years — three filed returns reviewed at onboarding
- Coordination with your other advisors — attorney, wealth manager, lender
- All personal returns — federal and every state you touch
- All entity returns — 1065, 1120-S or 1120, on Track B
- Quarterly estimates managed — recalculated, vouchers issued, safe harbour tracked
- Extensions — filed with a payment estimate, not a guess
- Notice handling — any IRS or state letter, answered, at no separate fee
- Examination representation — on returns we prepared
- Amendments — where they are worth filing
- Document vault — permanent, and yours whether or not you stay
Representation before the IRS is provided only by practitioners authorised under Circular 230, and outcomes in any examination or collection matter depend on your circumstances and on the agency’s determination. Nothing in this engagement is a guarantee of a particular tax result — what it guarantees is that someone competent is looking, all year.
What “dedicated” actually means here.
Most firms use the word. These are the commitments behind it, and they are in the engagement letter, not just on this page.
One business day
Every question gets a substantive answer within one business day — not an acknowledgement, an answer. If it needs research, you get the timeline that day.
Direct line, no gate
Your advisor’s direct number and email. No ticket queue, no general inbox, no re-explaining your situation to whoever picks up.
Deadline triage same day
Anything with a date on it — a notice, a closing, an exercise window — is read and answered the day it arrives.
A second who knows you
A named backup advisor reads your file too, so holidays, illness and filing season never leave you starting over.
Four quarters, four conversations.
The engagement has a rhythm, and it is the opposite of the usual one — the heavy thinking happens in the quiet months and April is mostly paperwork.
Filing
Returns prepared and filed. If the other three quarters were done properly, nothing here is news.
- All returns, federal and state
- K-1s chased on your behalf
- Q1 estimate set
Structure
The quiet quarter, and the one that moves the number most. Everything structural is cheapest to change now.
- Entity and election review
- Compensation reset
- Retirement plan design
Projection
Your year run forward to a written figure, with the levers still available listed against it.
- Mid-year projection issued
- Estimates re-cut
- Equipment and gains timing
Execution
The closing window. Everything agreed in Q3 gets done before the year shuts, with a checklist and a deadline each.
- Contributions funded
- Income and expense timing
- Distributions and bonuses set
Worth being honest about.
This is a significant annual commitment and it is not right for everyone. We would rather tell you that on the first call than in the second year.
- Your income is high enough that timing and structure move real money
- You own a business, or several, and the entity questions are live
- Equity compensation, real estate or investments make the year complicated
- You operate or earn in more than one state
- A sale, a purchase or a liquidity event is somewhere on the horizon
- You have been surprised by a tax bill more than once
- A straightforward return is genuinely all you need — take a filing package
- The business is new and not yet profitable — start with books and estimates
- You want a return prepared and no conversation. That is a fair thing to want.
- The main problem is a balance owed or unfiled years — start with Audit & Resolution
If any of these is you, we will say so and point you at the right thing. It costs us a sale and saves you a year.
Scoped, not listed.
The Standing File is an annual engagement, quoted after a scoping call, because the work genuinely differs — a two-state consultant and a six-entity group are not the same year. What we can promise is that the number is fixed for the term, agreed in writing before anything starts, and does not move because you called too often.
- Annual engagement, billed monthly or annually — your choice
- Fixed for the term. No hourly billing, no per-question charges
- Scope, deliverables and dates set out in a written engagement letter
- Includes the returns, so compare it against what you pay today in total
- Scoping call — 45 minutes, no charge. Your situation, honestly assessed.
- Second Look — we read your last three returns before quoting anything.
- Written proposal — scope, deliverables, named advisor and a fixed fee.
- Onboarding — file built, calendar set, first strategy session booked.
Nothing is billed until step three is signed.
Call me before you sign it. Afterwards I’m just a witness.