$2M+ savings per transaction
QSBS Sec 1202Long
Strategic QSBS saves $2M+ per transaction
Source: UncleKam
$3000 ordinary income offset
Tax-Loss HarvestingMulti
$3000/yr ordinary income offset
Source: encyclopedia
$75M gross asset threshold post-OBBBA
QSBS Sec 1202Long
$75M gross asset post-OBBBA was $50M
Source: Baker
180-day exchange close
1031 ExchangeMulti
180-day exchange completion
Source: encyclopedia
180-day rule
Opportunity ZonesMulti
180 days to invest gains into QOF
Source: encyclopedia
45-day identification rule
1031 ExchangeMulti
45-day identification rule
Source: encyclopedia
5-year rule each conversion
Roth StrategyMulti
5-year rule per conversion for early withdrawal
Source: encyclopedia
80% qualified active biz test
QSBS Sec 1202Multi
80% assets in qualified active biz
Source: SDOCPA
Active funds in tax-deferred
Asset LocationMulti
Active funds in tax-deferred (high turnover)
Source: encyclopedia
Algo TLH platforms
Tax-Loss HarvestingMulti
Wealthfront/Betterment algo TLH
Source: encyclopedia
Backdoor Roth IRA
Roth StrategyLong
Backdoor Roth - non-deductible IRA convert
Source: encyclopedia
Bonds in IRA / 401k
Asset LocationIncome
Bonds in tax-deferred (IRA / 401k)
Source: encyclopedia
Boot is taxable
1031 ExchangeShort
Boot (cash) is taxable
Source: encyclopedia
Both spouses SLAT reciprocal
SLATMulti
Both spouses establish SLATs - reciprocal trust risk
Source: encyclopedia
Bunching deductions
Donor-Advised FundsMulti
Bunching deductions in one year
Source: encyclopedia
C-corp required
QSBS Sec 1202Multi
C-corp required for QSBS
Source: SDOCPA
CRAT fixed annuity
CRTsMulti
CRAT fixed annuity
Source: encyclopedia
CRUT unitrust % each year
CRTsMulti
CRUT unitrust % of FMV each year
Source: encyclopedia
California decoupled CA tax
QSBS Sec 1202Short
California decoupled - taxes QSBS gains
Source: Millan
Charitable Remainder Trust
CRTsMulti
CRT - income for life remainder to charity
Source: encyclopedia
Crypto no wash-sale rule
Tax-Loss HarvestingMulti
Crypto no wash-sale rule (yet)
Source: encyclopedia
DAF tax-deduct contribution
Donor-Advised FundsMulti
DAF immediate tax deduction
Source: encyclopedia
Defer cap gains until 2026
Opportunity ZonesMulti
Defer cap gains by investing in QOF
Source: encyclopedia
Delaware Statutory Trust DST
1031 ExchangeMulti
DST for fractional 1031
Source: encyclopedia
Direct indexing for TLH
Tax-Loss HarvestingMulti
Direct indexing maximizes TLH opportunities
Source: encyclopedia
Donate appreciated stock
Donor-Advised FundsMulti
Donate appreciated stock no cap-gain
Source: encyclopedia
Donate appreciated stock direct
CharitableMulti
Donate appreciated stock direct to charity
Source: encyclopedia
Estate exclusion $13.99M 2025
EstateMulti
Estate exclusion $13.99M per person 2025
Source: encyclopedia
Estate exclusion lock-in
SLATMulti
Estate exclusion lock-in via SLAT
Source: encyclopedia
FEIE foreign earned income excl
InternationalMulti
FEIE $126500 2024 exclusion
Source: encyclopedia
FTC foreign tax credit
InternationalMulti
Foreign tax credit FTC for intl income
Source: encyclopedia
Fidelity Charitable largest
Donor-Advised FundsMulti
Fidelity Charitable largest DAF
Source: encyclopedia
GST tax exclusion
EstateMulti
GST exclusion for grandchildren
Source: encyclopedia
Grantor Retained Annuity Trust
GRATsMulti
GRAT - retain annuity remainder to heirs
Source: encyclopedia
HDHP required
HSAMulti
HDHP plan required for HSA
Source: encyclopedia
HSA invest stealth IRA
HSALong
Invest HSA - stealth retirement account
Source: encyclopedia
HSA triple-tax-advantaged
HSALong
HSA triple-tax-advantaged (deduct grow withdraw)
Source: encyclopedia
Holding period >1 yr LTCG
LTCG vs OILong
Hold >1 yr for LTCG
Source: encyclopedia
Index funds in taxable
Asset LocationLong
Index funds in taxable - low turnover
Source: encyclopedia
Inflation indexed 2027+
QSBS Sec 1202Long
Inflation-indexed for tax years after 2026
Source: Baker
Intentionally Defective Grantor Trust
IDGTMulti
IDGT - sale to grantor trust
Source: encyclopedia
LTCG rates 0/15/20%
LTCG vs OILong
LTCG rates 0/15/20% based on income
Source: encyclopedia
Lot-level identification
Tax-Loss HarvestingMulti
SpecID lot identification
Source: encyclopedia
Mega Backdoor Roth 401k
Roth StrategyLong
Mega backdoor Roth via 401k
Source: encyclopedia
Munis in taxable for tax-free
Asset LocationIncome
Munis in taxable for tax-free interest
Source: encyclopedia
NIIT 3.8% surtax
LTCG vs OIMulti
3.8% Net Investment Income Tax surtax
Source: encyclopedia
NIMCRUT make-up provision
CRTsMulti
NIMCRUT make-up of past shortfalls
Source: encyclopedia
NJ adopting Jan 1 2026
QSBS Sec 1202Long
NJ adopting QSBS Jan 1 2026
Source: Millan
Net Income CRUT NICRUT
CRTsMulti
NICRUT distributes lesser of unitrust or NI
Source: encyclopedia
OBBBA July 4 2025 changes
QSBS Sec 1202Long
OBBBA July 4 2025 expanded QSBS
Source: Surgent
OBBBA permanent estate exclusion
EstateMulti
OBBBA made $15M (indexed) estate exclusion permanent
Source: encyclopedia
Original issuance only
QSBS Sec 1202Multi
Must acquire at original issuance
Source: Surgent
Per-issuer cap $15M post-OBBBA
QSBS Sec 1202Long
$15M cap post-OBBBA was $10M
Source: SDOCPA
Pooled income fund
CharitableMulti
Pooled income fund alternative to CRT
Source: encyclopedia
Portability between spouses
EstateMulti
Portability of unused exclusion
Source: encyclopedia
Private foundation 5% min
CharitableMulti
Private foundation 5% min payout
Source: encyclopedia
Pro-rata rule trap
Roth StrategyShort
Pro-rata rule for Backdoor Roth
Source: encyclopedia
QOF Qualified Opportunity Fund
Opportunity ZonesLong
QOF investment vehicle for QOZ
Source: encyclopedia
QOZ + QSBS integration 2026
Opportunity ZonesLong
Integrate QOZ + QSBS for layered savings
Source: UncleKam
QOZ Sec 1400Z 2017 TCJA
Opportunity ZonesLong
Qualified Opportunity Zones from 2017 TCJA
Source: encyclopedia
QSBS Section 1202 exclusion
QSBS Sec 1202Long
Sec 1202 100% gain exclusion if held 5y
Source: UncleKam
QSBS made permanent
QSBS Sec 1202Long
OBBBA made QSBS permanent (no sunset)
Source: UncleKam
QSBS rollover Sec 1045
QSBS Sec 1202Long
Sec 1045 rollover within 60 days
Source: encyclopedia
Qualified Charitable Distribution QCD
CharitableMulti
QCD direct from IRA satisfies RMD
Source: encyclopedia
Qualified div LTCG rates
LTCG vs OILong
Qualified dividends - LTCG rates
Source: encyclopedia
Qualified intermediary required
1031 ExchangeMulti
Qualified intermediary required
Source: encyclopedia
REITs in tax-deferred
Asset LocationLong
REITs (ordinary div) in tax-deferred
Source: encyclopedia
Reverse 1031 acquire first
1031 ExchangeMulti
Reverse 1031 - acquire before sell
Source: encyclopedia
Rolling GRAT pre-IPO stock
GRATsLong
Rolling GRATs for pre-IPO stock
Source: encyclopedia
Roth = high-growth assets
Asset LocationLong
Roth IRA = highest-expected-return assets
Source: encyclopedia
Roth IRA tax-free withdrawal
Roth StrategyLong
Roth IRA tax-free withdrawal qual
Source: encyclopedia
Roth conversion bear-market
Roth StrategyLong
Roth convert in bear market - lower tax
Source: encyclopedia
Roth conversion early retirement
Roth StrategyLong
Convert during low-income early retirement
Source: encyclopedia
Roth conversion ladder
Roth StrategyLong
Roth conversion ladder over years
Source: encyclopedia
SPX index options 60/40
LTCG vs OILong
SPX options qualify 60/40
Source: encyclopedia
Sale to IDGT promissory note
IDGTMulti
Sale to IDGT for note - freeze estate
Source: encyclopedia
Save receipts strategy
HSALong
Save medical receipts for future tax-free withdrawals
Source: encyclopedia
Schwab Charitable second
Donor-Advised FundsMulti
Schwab Charitable second-largest DAF
Source: encyclopedia
Section 1031 like-kind real estate
1031 ExchangeLong
Sec 1031 1031 exchange RE only post-2017
Source: encyclopedia
Section 1035 exchange
AnnuitiesMulti
Section 1035 like-kind annuity swap
Source: encyclopedia
Section 1202 enacted 1993
QSBS Sec 1202Long
Section 1202 enacted 1993
Source: TaxAdviser
Section 1256 60/40 split
LTCG vs OIMulti
Section 1256 contracts 60/40 LTCG/STCG
Source: encyclopedia
Section 6166 estate inst payment
EstateMulti
Section 6166 - 14-yr installment for biz
Source: encyclopedia
Service biz disqualified
QSBS Sec 1202Short
Most service businesses disqualified
Source: SDOCPA
Spousal Lifetime Access Trust
SLATMulti
SLAT lock estate exclusion before 2026 sunset
Source: encyclopedia
Stacked QCD + DAF
Donor-Advised FundsMulti
Stack QCD + DAF strategies
Source: encyclopedia
Stacking with trusts
QSBS Sec 1202Long
Stacking QSBS exclusion with trusts
Source: encyclopedia
Step-up at death
1031 ExchangeLong
Step-up at death wipes deferred gain
Source: encyclopedia
Step-up basis at death
EstateMulti
Stepped-up basis to FMV at death
Source: encyclopedia
Step-up basis hold 10 yrs
Opportunity ZonesLong
10-yr hold = step-up to FMV (no tax)
Source: encyclopedia
Stocks in taxable for LTCG
Asset LocationLong
Stocks in taxable for LTCG rates
Source: encyclopedia
Substantially identical guidance
Tax-Loss HarvestingMulti
IRS substantially identical guidance
Source: encyclopedia
TLH cap gains offset
Tax-Loss HarvestingMulti
Tax-loss harvesting offset cap gains
Source: encyclopedia
Tax deduction PV remainder
CRTsMulti
Tax deduction PV charitable remainder
Source: encyclopedia
Tax-efficient asset location
Asset LocationMulti
Asset location - place tax-inefficient in tax-deferred
Source: encyclopedia
Tiered exclusion 3/4/5 yr 50/75/100%
QSBS Sec 1202Long
3yr 50% / 4yr 75% / 5yr 100% post-OBBBA
Source: Surgent
Vanguard Charitable
Donor-Advised FundsMulti
Vanguard Charitable third
Source: encyclopedia
Variable annuity tax-deferred
AnnuitiesMulti
Variable annuity tax-deferred grow
Source: encyclopedia
Walton zeroed-out GRAT
GRATsMulti
Walton zeroed-out GRAT cases
Source: encyclopedia
Wash sale 30-day rule
Tax-Loss HarvestingShort
Wash sale - 30 days substantially identical
Source: encyclopedia
An encyclopedia of publicly documented strategies for education. YCAI does not recommend, endorse, or trade any of these. Not investment advice.