HLP CAPITAL ADVISORY · READINESS REPORT ™

Tax Strategy
Readiness™.

Not tax advice. This is a 16-dimension coordination diagnostic that surfaces the highest-leverage tax moves your existing CPA and tax attorney should be evaluating — from entity elections and retirement architecture to timing strategy and QSBS positioning.

◉ 16 DIMENSIONS
◉ 12 STRATEGY MOVES
◉ VOICE-ENABLED
◉ 15-20 MINUTES
Not tax advice. Tax Strategy Readiness™ is a coordination diagnostic. HLP does not prepare returns, issue tax opinions, or represent clients before the IRS. Findings surface high-leverage moves for you to discuss with your existing CPA and tax attorney — those licensed professionals own the regulated advice and execution.
SECTION 01 · INCOME PROFILE 1 OF 16
◉ PROFILE · 01

Household income profile.

The income band drives which strategies produce material leverage. Under $250K, most sophisticated strategies produce marginal ROI. Above $500K, the leverage curve steepens rapidly.

◉ PROFILE · 02

Income composition.

W-2 income has limited flexibility. Business income opens entity-election strategies. Investment income opens loss-harvesting and carry-interest strategies.

◉ ENTITY · 01

Business entity structure.

Entity type drives self-employment tax exposure, deduction access, and retirement-plan eligibility. Wrong election costs 5-figures/year at $250K+ income.

◉ ENTITY · 02

Reasonable compensation.

For S-Corp owners, the balance between W-2 salary vs. K-1 distribution is a major SE-tax optimization — but the IRS scrutinizes low-comp filings.

◉ RETIREMENT · 01

Retirement architecture.

The single largest legal tax shelter for business owners. Most operators are running 401(k) or SEP when their income supports Solo 401(k), Cash Balance / Defined Benefit combinations that shelter $100K–$400K annually.

◉ POSITIONING · 01

Real estate tax positioning.

Real-estate professional status (REPS), cost-segregation studies, § 1031 exchanges, and short-term rental loophole are the four biggest real-estate levers. Most owners activate zero of them.

◉ POSITIONING · 02

Capital gains positioning.

Tax-loss harvesting, direct indexing, and charitable-remainder trusts can eliminate or defer six-figure gains. Timing matters — most owners realize gains reactively.

◉ POSITIONING · 03

Charitable strategy.

Direct-donation vs. donor-advised fund vs. charitable-remainder trust vs. private foundation — each has vastly different tax treatment, control, and timing benefits.

◉ POSITIONING · 04

§ 1202 QSBS posture.

Qualified Small Business Stock can eliminate up to $10M in federal gain per shareholder on a C-Corp exit — arguably the most powerful legal tax shelter in the code. Structure matters years before the sale.

◉ POSITIONING · 05

Estate + gift positioning.

The federal lifetime estate/gift exemption steps down significantly in 2026. Owners with $10M+ net worth who don't use exemption now may permanently lose it.

◉ POSITIONING · 06

State & domicile.

TX has no state income tax — a major structural advantage. But state PTE elections, multi-state nexus, and residency-audit exposure need coordination.

◉ TIMING · 01

Estimates & safe harbor.

Timing matters — over-withholding is an interest-free loan to the IRS; under-withholding triggers penalties. Safe-harbor discipline separates coordinated households from surprise-tax households.

◉ LEVERAGE · 01

Deduction leverage.

Home office · § 179 · bonus depreciation · Augusta Rule · accountable-plan reimbursements · vehicle. Business owners routinely leave 30-50% of legal deductions on the table.

◉ TIMING · 02

Upcoming events.

Sales, IPOs, marriages, inheritances, divorces, and material asset sales all create tax windows — most benefit from 12-24 months of pre-event positioning.

◉ COORDINATION · 01

CPA relationship.

The single best predictor of tax outcomes: proactive vs. reactive CPA. A proactive CPA saves the household 10-30× their annual fee. A filer-only CPA is a compliance cost.

◉ REPORT DELIVERY

Where do we send your report?

Chekelah's team reviews every submission within 48 hours. Your full Tax Strategy Readiness Report™ arrives as a signed PDF suitable for handoff to your existing CPA and tax attorney.

◉ SURFACING MOVES
—/100
SCORING

Your Tax Strategy Readiness score is being surfaced across the 12 highest-leverage moves your CPA should evaluate.

◉ TOP MOVES TO EVALUATE WITH YOUR CPA
DELIVERABLE
Full Tax Strategy Readiness Report™ arrives in 48 hours
Chekelah's Capital Advisory team reviews every submission. Report includes: full move-scored register, quantified potential leverage per move, questions to ask your existing CPA, and — if HLP identifies a CPA-relationship gap — introductions to DFW-based proactive-planning CPAs at your income tier.
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