Paying Expenses in Advance: The 12-Month Rule
October 4, 2026
The 12-month rule for prepaid expenses: what cash-method businesses can deduct, the limits for accrual businesses, prepaid interest, and year-end planning.
Read more →1,423 plain-English guides on cross-border moves, US and Canadian returns, and small-business money. Each one ends in what to do next, and says when a written Position Check is the smarter first step.
October 4, 2026
The 12-month rule for prepaid expenses: what cash-method businesses can deduct, the limits for accrual businesses, prepaid interest, and year-end planning.
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How carried interest and the management company are taxed for a small private equity or venture fund's principals: the carried interest as a profits interest taxed when the fund realizes gains, the three-year holding period under Section 1061 for long-term treatment, management fees as ordinary income to the management company, capitalized transaction costs versus broken-deal costs that only the management company can generally deduct, fund expenses, the net investment income tax, and the late K-1s that drive extensions and estimates.
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Entity structure and estimated taxes for principals of small private equity, venture, and search funds: the limited partnership fund, the general partner LLC that holds the carry, the management company and its S election, a separate carry vehicle for principals and employees, the operating agreements and vesting, estimated taxes on carry and fees when the K-1 arrives after the deadlines, the single-quarter exit, state sourcing, and qualified small business stock through the fund.
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Private foundation excise taxes: the 1.39 percent tax on net investment income, self-dealing under Section 4941 and its absolute ban on insider transactions, the 5 percent minimum distribution requirement, excess business holdings, jeopardizing investments, taxable expenditures and expenditure responsibility, Form 990-PF, and the donor-advised fund alternative.
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Purchase price allocation under Section 1060: the residual method, the seven asset classes, Form 8594, how buyers and sellers are taxed on each class, and allocation agreements.
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QSEHRA versus ICHRA: eligibility, annual limits, employee classes, notices, the effect on premium tax credits, owner participation, and how to choose.
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Qualified small business stock under Section 1202: C corporation and original issuance requirements, the active business test, the 2025 changes to the asset threshold and exclusion cap, tiered holding periods, and excluded industries.
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The research and development tax credit for small businesses: the four-part test, qualified research expenses, the payroll tax offset, Form 6765, and Section 174A expensing.
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Entity structure and estimated taxes for real estate developers: a separate LLC for each project, investor members with a preferred return and the developer's promote as a profits interest, the development company that earns fees and holds the staff, construction lender requirements and personal guarantees, estimated taxes when lot closings and home sales cluster, the at-risk and passive rules for investors, keeping long-held investment land out of the dealer entity, and the exit at build-out.
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Tax rules for real estate developers and land subdividers: lots and homes held for sale as inventory producing ordinary income, capitalization of land, entitlement, infrastructure, interest, and property taxes during development under Section 263A, allocating common improvement costs across lots, the alternative cost method, dealer status and the loss of capital gain, installment sale, and 1031 treatment, the Section 1237 exception for investors, impact fees and permits, completed contract accounting for home construction, and Florida documentary stamp taxes.
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Real estate professional status under Section 469(c)(7): the 750-hour and more-than-half tests, material participation in rentals, the aggregation election, spouses, time logs, the $25,000 allowance alternative, and the net investment income tax.
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Related-party transactions under Section 267 and related rules: who is related, the loss disallowance on sales, the matching rule that defers accrued expenses to a related cash-method payee, Section 1239 ordinary income on depreciable property, Section 707(b) for partnerships, installment sales to related parties, and documenting arm's-length terms.
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Relocating a business to another state: domestication versus forming a new entity, keeping the EIN and tax history, final returns and withdrawals in the old state, registrations in the new state, payroll transitions, the trailing nexus that follows a move, apportionment in the year of the move, deductibility of moving costs, and relocating to Florida.
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Remote employees in other states: state withholding and the employee's resident state, unemployment insurance localization rules, reciprocity agreements, convenience-of-the-employer states, income and sales tax nexus, workers' compensation, and the Florida employer with out-of-state staff.
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Rental property taxation: Schedule E income and expenses, 27.5-year depreciation, repairs versus improvements and the safe harbors, passive loss limits and the $25,000 allowance, the qualified business income safe harbor, and depreciation recapture at sale.
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Retirement plan startup credits under SECURE 2.0: the startup cost credit up to $5,000 a year for three years, the employer contribution credit up to $1,000 per employee over five years, the automatic enrollment credit, eligibility, Form 8881, and the no-double-benefit rule.
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Rollovers as business startups explained: the C corporation and new 401(k) plan structure, how the plan buys company stock, no distribution or penalty, ongoing requirements (employee coverage, Form 5500, valuation, reasonable salary), prohibited transaction risk, IRS scrutiny, and alternatives like plan loans.
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Roth conversions for business owners: taxed as ordinary income, bracket filling in a low-income year, startup losses and net operating losses, the effect on the qualified business income deduction, Medicare premiums and marketplace credits, the five-year rules, paying tax from outside funds, and state timing.
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RSU withholding after moving from the U.S. to Canada: why both U.S. and Canadian payroll withhold on the same vest, workday sourcing under the treaty, Canadian taxation of RSUs as employment income, recovering excess U.S. and Canadian withholding, and the T1213 waiver.
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The S corporation late-filing penalty: how it is calculated per shareholder per month, late K-1 penalties, extensions, first-time abatement, and reasonable cause.
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How S corporation owners set a reasonable salary: the IRS factors, the three valuation approaches, what happens if you pay too little, and how to document it.
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How S corporation shareholder basis works, the ordering rules, debt basis, the accumulated adjustments account, and when Form 7203 must be filed.
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SaaS bookkeeping and revenue recognition: recognizing subscriptions ratably and recording deferred revenue, annual prepayments, monthly recurring revenue and churn, capitalizing sales commissions, research and development costs, sales tax on software by state, stock compensation, the difference between book revenue and tax revenue, and the advance payment deferral.
Read more →October 4, 2026
Sales tax nexus after Wayfair: physical and economic nexus, the $100,000 and transaction thresholds, marketplace facilitator laws, taxability of services and software, registration and filing, voluntary disclosure, and Florida's rules.
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