RESEARCH.md: tax strategy landscape (offset/deferral/charitable taxonomy)

This commit is contained in:
Greg Pomerantz 2026-08-27 20:15:15 -04:00
parent 895efc9bff
commit 499ae5813d

View File

@ -639,3 +639,46 @@ project (fundlab/overnight.log, fundlab/universe_cache/), and use
- 2026-08-27 03:23 === overnight run finished in 5.2h ===
- 2026-08-27 03:24:06 watchdog: process gone but screen COMPLETE (0 missing) - watchdog exiting
- 2026-08-27 03:24:06 watchdog: watchdog exit
### Tax strategy landscape (2026-08-27)
Full taxonomy of security types / structures that offset capital gains
or ordinary income, in service of the tax-placement work:
1. **Offset cap gains (taxable):** loss harvesting (1:1 + $3k/yr +
carryfwd; tricks: write options after harvest = no wash sale; munis
are 1091-exempt so harvest+rebuy same day; loss-harvester ETFs);
fund-level harvest reserve (already modeled); §1256 CTA MTM (60/40
character, losses included); §1244 stock (ordinary loss
$50k/$100k MFJ).
2. **Offset ordinary income (K-1/depreciation world):** MLP (ROC ->
investor LTCG; loss pass-through is real but basis/at-risk/passive
limited; OBBBA 199A 20% on MLP income 2025-2029; IRA UBTI check,
many are 531(e)(2)-free); real estate depreciation (100% bonus now
permanent post-OBBBA; $25k active-participant loss phasing out
$100-150k MAGI; unlimited w/ REP 500-hr status; working-farm 1031;
199A on real property SALE gains 2025-2029); 45L/59A direct-pay LLCs
(30% credit + basis depreciation -> current deduction ~1.5-2x
investment, 30-yr/15-yr holds); private credit K-1s; 199A generally.
3. **Inherently favorable income:** munis (NIIT-exempt, no wash sale,
muni-equivalents for out-of-state); QREIT dividends (20% LTCG rate);
Opportunity Zone funds (deferral + 100% excl. on post-2018 apprc,
2026 last year for current designations; taxable-only); QSBS 1202
(100% excl., $10M/issuer, 5yr); §1256 gains.
4. **Charitable/structural:** donate appreciated LTCG (skip gain + FMV
deduction; DAF timing); CRT (sell concentrated pos. untaxed); QCD
(70.5+, IRA->charity excluded from income, counts to RMD - the one
way to AVOID a trad IRA's ordinary character); 1031 (real property
only); gifting LTCG stock (carryover basis, lower-bracket donee,
~$19k/yr exclusion).
5. **Deferral outside IRA:** annuities (only other deferral bucket;
no RMD; 10% penalty pre-59.5).
Fit for this portfolio (mutual-fund investor, taxable + trad IRA):
(1) harvest discipline incl. before conversion/RMD years, (2) munis
(109 in screen), (3) small CTA sleeve (taxable), (4) K-1/depreciation
overlay only as a separate private-markets decision, (5) charitable
when relevant. All of 3-4 above are taxable-only by nature.
Post-OBBBA (Pub. L. 119-21) items I could not re-verify live (SearXNG
index down): 199A specified-investment-asset scope/sunset, SALT cap,
QCD dollar limit. Verify with tax pro before relying.