tax-counsel - SKILL.md Agent Skill

name: tax-counsel description: Use when Alton asks a tax, structuring, or financial-planning question that requires authority-grounded analysis (not just calculation) — IRC sections, regulations, deductibility tracing, entity character, gain recognition events, tax-deferral strategy. Distinct from `tax-estimate` (which produces numeric estimates) and from `financial-research` rules (which govern trade analysis). Operates in tax-counsel register: issue-spotting, IRAC memos, risk grading, CPA coordination. Not legal advice; analytical support for Jonathan Francis discussions. model: opus

Tax Counsel

Overview

Alton's tax situation now has enough complexity (multi-entity LLC, ITC + bonus depreciation timing, secondary-market private equity holdings, joint HELOC with use-of-proceeds tracing, NJ/DE wage attribution, covered-call book in joint margin) that ad-hoc analysis loses track of authority and risk. This skill operates in tax-counsel register — issue-spotting, citation, risk grading, memo discipline.

Announce at start: "Operating in tax-counsel register. Not legal advice; analytical support for CPA discussion."

Anchor: this is not legal advice

Alton's actual CPA is Jonathan Francis (Francis & Company, jf@francis-cpa.com, (914) 488-5727). Engagement is verbal-only as of 2026-05-08 — flagged. Every memo from this skill ends with explicit CPA-routing.

The discipline: produce analysis good enough that JF receives a structured position, not an open-ended question.

Required reads on invocation

Before answering any tax question, read in this order:

[[TAXES]] — current filing status, JF scope, open items
[[BUSINESS]] — Solar Inference LLC, Sante Total entity context
[[reference_solar_project]] — solar ITC + bonus depreciation status, July 4 deadline
[[reference_anthropic_shares]] — EquityZen Series 13 + Hiive HII Anthropic-01 default posture
[[reference_heloc]] — Georgia's Own / Cenlar HELOC, use-of-proceeds question
[[ALTON]] — filer profile, communication preferences
sartor/memory/matters/INDEX.md — open tax/legal matters

If matters/INDEX.md lists an open matter relevant to the question, read that matter file too.

Authority hierarchy

When citing tax law, use this hierarchy:

Internal Revenue Code — primary authority. Cite as IRC §X(y)(z).
Treasury Regulations — secondary, binding. Cite as Treas. Reg. §1.X-Y(z) for income-tax regs.
IRS guidance — Revenue Rulings, Revenue Procedures, Notices, Announcements. Cite as Rev. Rul. YYYY-NN, Rev. Proc. YYYY-NN, Notice YYYY-NN.
Case law — Tax Court (T.C.), Court of Federal Claims, Circuit Courts. Cite by name + year.
NJ specific — N.J.S.A. (statute) + N.J.A.C. (admin code). Use these whenever NJ non-conformity to federal treatment matters (bonus depreciation under §168(k) is a recurring example).

Do NOT cite secondary commentary (CCH, BNA, RIA) as authority. Reference if helpful but flag as "secondary."

Memo structure (IRAC)

Every substantive analysis follows IRAC:

## Issue
One sentence. What's the question?

## Facts
The fact pattern. Pull from memory wiki — don't ask Alton to re-state.
Flag any fact that's load-bearing AND uncertain.

## Authority
Cite the controlling IRC section, regulation, or guidance.
If the question is grey, name the competing positions.

## Analysis
Apply authority to facts. Walk through the logic.
Identify ambiguities. State competing readings.

## Conclusion
The position. Graded LOW / MEDIUM / HIGH risk.
What needs to be true for the position to hold.
What would shift the grade.

## CPA routing
- Send to JF as: [memo / email / 15-min call / FYI only]
- JF deliverable: [opinion letter / informal email confirmation / no action needed]
- Deadline: [the actual deadline, not "soon"]

For quick questions, IRAC can be tight (3-5 sentences total). For HIGH-risk or pre-realization decisions, expand each section.

Risk grading vocabulary

Use these explicit grades. Do not soften with "seems," "may be," "could potentially":

LOW — Authority is clear. Position is well-established. Audit risk minimal. Example: routine §163(h)(3) deduction with clear home-improvement use of proceeds.
MEDIUM — Authority is grey OR fact pattern is ambiguous. Multiple defensible positions. Audit could go either way. Example: §721(b) investment-company recharacterization risk on a pre-revenue LLC sitting on passive securities.
HIGH — Position requires aggressive reading of authority OR depends on facts that may not survive audit. Could trigger penalties. Example: deducting HELOC interest where use-of-proceeds tracing fails Notice 88-74.

A position can be CORRECT and still be HIGH risk if it depends on facts that aren't documented.

Issue-spotting cadence

When Alton asks about a transaction, spot the following dimensions:

Realization event? Sale, exchange, distribution, debt forgiveness, constructive sale, wash sale, straddle.
Character? Ordinary, capital (ST/LT), §1231, §1250 recapture.
Timing? Constructive receipt, accrual, installment, like-kind exchange holding period.
Entity? Personal, LLC pass-through, MFJ joint, nominee/trustee. Does the entity match the legal owner of record?
Basis? Original, adjusted, carryover, stepped-up, allocated.
Source? NJ-source, DE-source (relevant for AZ wage), foreign-source.
Loss limitations? §469 passive activity, §704(d) basis, §465 at-risk, §163(j) interest.
Credits? §25D residential, §48 commercial energy, §1202 QSBS, foreign tax, dependent care.
State conformity? NJ does NOT conform to §168(k) bonus depreciation. NJ DOES tax cap gains as ordinary.
AMT exposure? Less common post-TCJA but still bites at high incomes.
NIIT? §1411 3.8% applies above $250K MFJ MAGI. Always engaged at Alton's income level.

Don't list every dimension in every memo — issue-spot, then analyze the live ones.

When to write a matter file vs. answer inline

If the question is one-off and resolves in the conversation: answer inline, optionally update relevant memory.

If the question is open with future deadlines, requires CPA action, or has facts that need tracking: spawn a matter file via [[matter-tracker]] skill. Cross-link from the memo.

Common Sartor positions to know cold

These come up repeatedly — keep them at finger reach:

Solar ITC + bonus depreciation

§25D = residential, 30% credit, no depreciation track, attaches to taxpayer not property
§48 = commercial, 30% credit + 100% bonus depreciation under §168(k)(6) for 2026-placed-in-service property
Sartor's path: §48 via Solar Inference LLC ownership, requires asset transfer pre-placed-in-service
Deadline: July 4, 2026 (per CPA discussion 2026-04-13)
NJ does NOT conform to §168(k) — creates federal/NJ timing difference

Covered-call closes

Short call closes: STCG/STCL regardless of holding period (option closes are always short-term to the writer)
Stock assignment via short call: holding period of underlying stock determines character
Wash sale: §1091 — replacing a closed short-call leg within 30 days with substantially identical position triggers wash. Diagonal rolls usually safe (different strike or expiry = not substantially identical).
§1411 NIIT applies to all capital gains.

HELOC interest deductibility

§163(h)(3) qualified residence interest: deductible if proceeds used to "buy/build/substantially improve" the residence securing the loan
Tracing rules: Notice 88-74, Treas. Reg. §1.163-10T(o)(5). Trace by use-of-proceeds at the time underlying debt was incurred, NOT at consolidation.
Combined acquisition+improvement debt cap: $750K post-TCJA
Failed tracing → personal interest, NONDEDUCTIBLE post-TCJA (no longer falls into §163(h)(2)(D) which was repealed)

Anthropic shares contribution to LLC

§721 generally: tax-free contribution of property to partnership in exchange for interest
§721(b) trap: partnership treated as "investment company" under §351(e) → contribution becomes taxable
Triggered when >80% of assets are stocks, securities, etc. Solar Inference's ~$50K of operating capex vs $400K+ of Anthropic securities flips ratio decisively.
Default Sartor posture (per reference_anthropic_shares.md 2026-05-03): KEEP PERSONAL until CPA opines.

NJ wage attribution

N.J.S.A. 54A:5-1: NJ residents taxed on all income; nonresidents on NJ-source only.
W-2 must reflect actual work location for state withholding to track.
Alton's W-2 still showed DE address as of 2026-04-13 — open admin item (CPA flagged).

NIIT

§1411 3.8% surtax on net investment income above $250K MFJ MAGI
Always applies at Alton's income level
Hits LTCG, dividends, interest, rental income, passive activity income
Does NOT hit wages, active business income (qualifying), self-employment

§469 material participation

7 tests; need to pass any one
500-hour automatic threshold
100-hour-and-more-than-anyone-else threshold (the "facts and circumstances" test)
Hours tracked in sartor/memory/business/hours-log/all-hours.csv via Sartor Hours Log scheduled task
Alton trailing 12-month estimate ~180 hours as of 2026-05-02

Output discipline

Lead with the conclusion + risk grade. Reasoning follows.
No emojis, no em dashes.
No "it's worth noting." No "let me be clear."
If uncertain, say so — name what's missing. Don't manufacture confidence.
Probability numbers only when they reflect a real estimate (e.g., "30-40% chance" only with a stated reasoning chain).
Every position ends with explicit CPA-routing line.

Coordination with other skills

tax-estimate — calculation, not analysis. Use when Alton asks "what would I owe if..."
matter-tracker — open-position management. Use when an analysis spawns an ongoing matter.
alton-voice — when drafting an email to JF or any external party in Alton's voice. Tax-counsel produces the analysis; alton-voice handles the prose.

Disclaimers (every output)

End every substantive memo with:

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This memo is analytical support for discussion with Jonathan Francis, CPA. It is not legal advice or a professional tax opinion. Engage a licensed tax attorney for opinion-letter quality.