This is the realistic retirement play for MVHP at its current size. A 401(k) Safe Harbor plan allows Nicki and Michael to max personal contributions ($23K each in 2026, $30.5K if 50+) without failing non-discrimination testing. Cost: a 3-4% safe harbor match for participating employees. For 20 employees with ~60% participation at $40K average comp, employer match cost is roughly $15-25K/year. In exchange you get ~$50K combined personal pre-tax shelter (more if 50+).

The cost-benefit is real but not slam-dunk: you spend roughly $15-25K to shelter ~$50K. The personal tax saved on $50K at your bracket (~32-37% federal + 6.75% MT) is roughly $20-22K. The employer match cost is a real expense to MVHP, but it is also a deduction. Net benefit depends on your actual numbers.

Ask CPA: Run the 401(k) Safe Harbor cost-benefit with current employee comp data. Compare a 3% non-elective vs 4% match design. Recommend a TPA (Guideline, Vestwell, Human Interest are common low-cost options for businesses your size).

Technically available but requires equal % contribution to all eligible employees. If you contribute 25% of comp for yourself, you contribute 25% for all 20 employees. For ~$40K average employee comp, that is roughly $200K/year of employer cost to shelter ~$70K of your own income. The math doesn't work. Skip unless you want to be very generous with employee retirement (which you don't).

Same non-discrimination wall as SEP. Can be designed with cross-tested allocations to favor owners, but requires actuarial fees ($5-10K/year), still requires meaningful employee contributions, and only pencils if owner comp is very high relative to employee comp. For a 20-person S-Corp, usually not worth the complexity unless you want to commit to large, predictable retirement contributions for many years. Worth running with CPA only if you have a specific reason to want $100K+/year of additional shelter beyond a Safe Harbor 401(k).

Auxil currently has no employees beyond Nicki (and possibly Michael). A Solo 401(k) is theoretically available on the Auxil side IF Auxil stays owner-only. BUT controlled-group rules under IRC §414(b)/(c) may aggregate MVHP and Auxil for ERISA non-discrimination testing if Nicki owns >80% of both. If they aggregate, MVHP's 20 employees count against Auxil too, which kills the Solo 401(k) eligibility. This is a question only your CPA can answer based on actual ownership percentages.

Ask CPA: Are MVHP and Auxil a controlled group for ERISA purposes? If not, what is the sheltering opportunity through an Auxil Solo 401(k)?

Once Auxil is a Delaware C-Corp held for 5+ years, IRC §1202 (Qualified Small Business Stock) lets you exclude up to $10M of capital gains on sale, federal tax-free. This is the single biggest tax break in the code for founders. The clock starts when stock is issued, so the longer you wait to convert, the longer you wait to start the 5-year clock. Conversion timing matters.

Also: Delaware corporate law is preferred by virtually every institutional investor. Combined benefit makes the Stripe Atlas conversion a clear move.

Ask CPA + startup tax specialist: Conversion timing relative to first SAFE / priced round. Document fair market value at conversion. Make sure stock is "qualified" (active business, <$50M gross assets at issuance).

The R&D credit needs three buckets to add up: wages of people doing qualified research, contract research costs, and supplies (cloud, API, infrastructure). Auxil currently has none of the first two. Nicki is not on Auxil's W-2 payroll yet, and "Big C" is Claude Desktop (an Anthropic tool subscription), not a billable contractor. That leaves only supplies: Anthropic API/subscription, DigitalOcean for Auxil, hosting; realistically $1K to $5K per year right now.

The Alternative Simplified Credit on a brand-new business is 6% of qualified spend in year 1. On a $1-5K pool, that is $60 to $300. The documentation overhead and Form 6765 filing cost more than the credit returns. Skip for 2026.

When this becomes worth chasing: the moment Nicki or Michael go on Auxil's W-2 payroll, OR Auxil hires a third-party developer, OR Auxil's infrastructure spend scales materially. Any of those expands the QRE pool significantly. Until then, defer.

The bigger Auxil tax play is QSBS, not R&D. Section 1202 via Stripe Atlas Delaware C-Corp conversion is where the seven-figure tax break lives for founders. Prioritize that conversation with the CPA over the R&D credit.

Ask CPA: Defer R&D credit analysis until Auxil has W-2 payroll. Confirm the deferral does not forfeit any year-1 election rights.

You are already deducting the Escalade for business use. The recommendation here is maintenance: verify with Jordahl & Sliter that the business-use percentage is being documented annually with a current mileage log, and that the §179 / bonus depreciation election was set up correctly at acquisition. The audit defense lives in the mileage log; if you do not have one currently running, start one (MileIQ, Everlance) so 2026 has solid contemporaneous records.

Ask CPA: Confirm Escalade depreciation schedule is on track. Verify business-use percentage for 2026. Recommend a mileage tracking method if not already in place.

Michael needs a new truck in 2026, which is a fresh first-year deduction opportunity. Vehicles with GVWR over 6,000 lbs qualify for accelerated depreciation. Most full-size trucks meet this: F-250 and up, Silverado 2500 and up, Ram 2500 and up, Tahoe, Suburban, Yukon, Sequoia, Tundra. Year-1 deduction can be $25K-$30K+ depending on vehicle price, business-use percentage, and bonus depreciation rules in effect for 2026 (currently 20% bonus, may change with legislation).

Tactical considerations: time the purchase based on bonus depreciation rules at the time. Document business use from day one (mileage log, named business driver, business-use insurance rider if applicable). Avoid sub-6,000-lb trucks (smaller F-150s in some configurations) which fall under the much smaller passenger-vehicle depreciation cap.

Ask CPA: What is the optimal purchase timing in 2026 to maximize §179 + bonus depreciation? Confirm GVWR > 6,000 lb on the specific truck Michael is considering. Confirm the deduction calculation given expected business-use percentage.

This is the strongest remaining lever NOT constrained by employee count. The election allows MVHP (an S-Corp) to pay Montana state income tax at the entity level, federally deductible without the $10K SALT cap on Schedule A. For a $6-7M business with $1M+ of taxable income flowing to Nicki and Michael, the federal benefit can be $5-15K/year. This is a near-pure-win move requiring just an annual election filing. Should be the first thing confirmed in the CPA conversation.

Ask CPA: Confirm Montana PTET applicability for MVHP. File the election for 2026 if not already filed. Election deadline timing matters (typically by extended due date of return).

If you hold appreciated public stock, donate it to a Donor-Advised Fund (Fidelity Charitable, Schwab Charitable, Vanguard Charitable). You avoid the capital gains tax on the appreciation AND get a full FMV deduction. Strategy: bunch multiple years of charitable giving into one big DAF contribution year for itemization advantage, then grant out from the DAF over multiple years to your usual causes (Whitefish Band Boosters, Bulldog Booster Club, etc.). Especially powerful if Auxil eventually has a liquidity event and you have appreciated assets to redirect.

Ask CPA: Identify any appreciated public stock positions worth donating. Assess itemization vs standard deduction crossover for current year.

Once Auxil is a real entity with revenue and a board, the same §280A(g) rule applies. You get another 14 days of tax-free home rental, this time deductible to Auxil. Effectively doubles the annual benefit (28 days total across both entities). Caveat: the meetings need to be defensibly Auxil-specific, not pretextual. Different agendas, different attendees if appropriate, different decisions.

Ask CPA: When Auxil reaches enough operational maturity (post-revenue, post-board), add it to the Augusta strategy. For 2026, MVHP only.

A cost seg study reclassifies certain components of a building (carpet, fixtures, landscaping, electrical) from 27.5/39-year depreciation into 5/7/15-year accelerated buckets. For a home office in a $2M+ home, the accelerated depreciation can shift $20-40K of deductions into early years (tax deferral, not absolute savings). For commercial property, the benefit can be much larger.

Ask CPA: Whether a cost seg study makes sense given your specific properties. Most studies pay for themselves at >$500K basis.

MVHP is an S-Corp, so health insurance premiums for 2%+ shareholders (Nicki and Michael) can be deducted above-the-line. Requires specific payroll treatment: premiums are paid through the company, included in W-2 Box 1 wages, and then deducted personally on Schedule 1. Most CPAs handle this correctly but worth confirming since the savings are real every year.

Non-discrimination caveat (20-employee context): Health benefits offered to officers must be offered on equivalent terms to other eligible employees, OR structured as an HRA that meets safe harbor rules (QSEHRA or ICHRA). For MVHP at 20 employees, you almost certainly already offer some level of group health coverage to staff, in which case Nicki/Michael's premiums get the standard above-the-line treatment without additional complexity. The wrinkle is only if you DON'T offer employee health currently and want to claim the officer deduction, which would create a non-discrimination problem.

Ask CPA: Confirm current group health setup is optimized for the S-Corp shareholder deduction. Verify W-2 reporting and payroll coding.

If you have a dedicated home office space used regularly and exclusively for business, the home office portion of the property is deductible. With a 7,000 sq ft home, even 200-300 sq ft for office space is 3-4% of expenses (utilities, insurance, repairs, depreciation) deductible. Modest but free money once set up. Note: the simplified method ($5/sq ft, max 300 sq ft) caps at $1,500. The actual-expense method usually wins for a property of your size.

Ask CPA: Set up the actual-expense home office calculation. Confirm what counts as "regular and exclusive use" for audit defense.

Michael is already an officer at MVHP per our file. Confirm his comp is reasonable for the work he does (audit defense), and that he has access to the same retirement plan structures Nicki does. Roth IRA / Roth 401(k) contributions on his side broaden the tax-shelter footprint.

Ask CPA: Review Michael's comp for reasonableness benchmark, confirm both spouses are maxing out applicable retirement plans.