Insights & Resources

Advanced Tax Planning

Tax planning is where most of the measurable value in a financial plan shows up. These articles walk through the mechanics behind Roth conversions, the QBI deduction, the OBBBA changes, charitable giving, and real estate taxation, so you can see how each rule actually works before deciding whether it applies to you.

Charitable Remainder Trusts

Advanced Tax Planning

Charitable Remainder Trusts: The Mechanics, the Math, and the Traps

How a charitable remainder trust works: selling appreciated assets tax-deferred, the CRUT vs. CRAT choice, the four-tier payout rules, and the 2026 changes.

Jim Crider, CFP®
15 min readSep 4, 2026

Opportunity Zones After OBBBA

Advanced Tax Planning

Opportunity Zones After OBBBA: The 2027 Rules, the 2026 Deadline, and the New Rural Tier

OBBBA made Opportunity Zones permanent with new rules starting 2027: rolling five-year deferral, a 30% rural step-up, tighter maps, and a 2026 bill coming due.

Jim Crider, CFP®
16 min readAug 31, 2026

Depreciation Recapture

Advanced Tax Planning

Depreciation Recapture When You Sell a Rental: The Layers, the Math, and the Traps

How recapture is actually calculated when you sell a rental: the gain layers, the 25% ceiling, installment and 1031 traps, and the one exit that erases it.

Jim Crider, CFP®
13 min readAug 29, 2026

The Passive Activity Loss Rules

Advanced Tax Planning

The Passive Activity Loss Rules: Why Rental Losses Get Trapped, and the Four Ways Out

How Section 469 traps rental losses, how the $25,000 allowance phases out, what real estate professional status requires, and when suspended losses release.

Jim Crider, CFP®
20 min readAug 28, 2026

The Short-Term Rental Exception

Advanced Tax Planning

The Short-Term Rental Exception: How Material Participation Turns Rental Losses Non-Passive

How the seven-day rule and material participation let short-term rental losses offset W-2 income, why cost segregation pairs with it, and where it goes wrong.

Jim Crider, CFP®
19 min readAug 27, 2026

The Backdoor Roth IRA and the Pro-Rata Rule

Advanced Tax Planning

The Backdoor Roth IRA and the Pro-Rata Rule: The Two-Step Everyone Does and the Math Almost Nobody Checks

How the backdoor Roth IRA works in 2026: the two steps, the pro-rata rule that taxes it, the December 31 test, Form 8606, and the cleanup moves.

Jim Crider, CFP®
11 min readAug 26, 2026

Tax-Loss Harvesting and the Wash Sale Rule

Advanced Tax Planning

Tax-Loss Harvesting and the Wash Sale Rule: What the Brokerage Button Doesn't Tell You

How tax-loss harvesting works: the 61-day wash sale window, the basis adjustment, the IRA trap, and when a harvest costs more than it saves.

Jim Crider, CFP®
19 min readAug 22, 2026

TSP Roth In-Plan Conversions

Advanced Tax Planning

TSP Roth Conversions: The In-Plan Feature Is Live, and It Changes the Playbook

The TSP now allows Roth conversions inside the plan. The mechanics, the two five-year clocks, and how to decide in-plan versus roll-to-IRA.

Jim Crider, CFP®
11 min readAug 18, 2026

Estimated Taxes and the Safe Harbor

Advanced Tax Planning

Estimated Taxes and the Safe Harbor: The Cheapest Money on the Tax Calendar

The three safe harbors, the four deadlines that aren't quarters, and how the safe harbor decision fits into multi-year tax planning.

Jim Crider, CFP®
11 min readAug 13, 2026

The Multi-Year Tax Projection

Advanced Tax Planning

The Multi-Year Tax Projection: How Lifetime Tax Planning Actually Works

What a multi-year tax projection actually contains, the two yardsticks it runs on, and why single-year tax optimization quietly loses.

Jim Crider, CFP®
13 min readAug 10, 2026

The 0% Capital Gains Bracket

Advanced Tax Planning

The 0% Capital Gains Bracket: How Tax-Gain Harvesting Works in 2026

How the 0% long-term capital gains bracket works in 2026: the stacking math, tax-gain harvesting mechanics, and the traps that make 'free' gains costly.

Jim Crider, CFP®
12 min readAug 6, 2026

Net Unrealized Appreciation (NUA)

Advanced Tax Planning

Net Unrealized Appreciation: The 401(k) Employer Stock Tax Break

How NUA works in 2026: the lump-sum rules, triggering events, the basis-to-gain math, and when rolling 401(k) employer stock to an IRA costs you.

Jim Crider, CFP®
12 min readAug 5, 2026

Qualified Charitable Distributions

Advanced Tax Planning

Qualified Charitable Distributions: QCD Rules, Traps, and Paperwork

How to execute a QCD correctly: first-dollars-out timing, eligible charities, the one-time $55,000 election, reporting, and the traps that blow the exclusion.

Jim Crider, CFP®
9 min readAug 3, 2026

The Roth Conversion Ladder

Advanced Tax Planning

The Roth Conversion Ladder: Funding Early Retirement Before 59½

How the Roth conversion ladder works: five-year clocks, the bridge years, sizing each rung, and the trade-offs early retirees should model.

Jim Crider, CFP®
10 min readJul 31, 2026

The Roth Five-Year Rules

Advanced Tax Planning

The Roth Five-Year Rules: Two Clocks, Two Purposes, One Common Trap

How the two Roth five-year rules actually work: the contribution clock, the conversion clock, the Roth 401(k) rollover trap, and what changes at 59½.

Jim Crider, CFP®
12 min readJul 29, 2026

How Trump Accounts (530A) Work

Advanced Tax Planning

How Trump Accounts (530A) Work, and the Roth Conversion Most Get Wrong

Trump Accounts launched July 4, 2026. How the 530A account works: the $1,000 deposit, the $5,000 cap, Form 4547, and the Roth caveats most coverage skips.

Jim Crider, CFP®
16 min readJul 27, 2026

The $15 Million Estate Tax Exemption

Advanced Tax Planning

The $15 Million Estate Tax Exemption: What Permanence Actually Changes About Estate Planning

The exemption is $15 million per person, permanent, and indexed. For most families that changes what estate planning is for: basis, portability, and control.

Jim Crider, CFP®
13 min readJul 24, 2026

Turning Your Home Into a Rental

Advanced Tax Planning

Turning Your Home Into a Rental: The Three-Year Tax Window Most Owners Never Knew They Had

Convert your home to a rental and the $500,000 home-sale exclusion starts a countdown. The three rules, the three-year window, and the rent-vs-sell framework.

Jim Crider, CFP®
15 min readJul 14, 2026

The HSA as a Stealth Retirement Account

Advanced Tax Planning

The HSA as a Stealth Retirement Account: The Only Triple-Tax-Advantaged Account in the Code

The HSA is the only account that's untaxed going in, growing, and coming out. The 2026 rules, the receipts strategy, what changes at 65, and its one weakness.

Jim Crider, CFP®
18 min readJul 9, 2026

The Mega Backdoor Roth

Advanced Tax Planning

The Mega Backdoor Roth: How High Earners Can Put Up to $72,000 a Year Into Retirement Accounts

Your 401(k) limit isn't $24,500. It's $72,000. How after-tax contributions plus prompt Roth conversion unlock tens of thousands a year of tax-free growth for high earners.

Jim Crider, CFP®
15 min readJul 6, 2026

Charitable Giving in 2026

Advanced Tax Planning

Charitable Giving in 2026: Donor-Advised Funds, Bunching, and the New Math of Tax-Efficient Generosity

How to give to charity tax-efficiently in 2026 — donor-advised funds, the bunching strategy, donating appreciated stock, qualified charitable distributions, and what the One Big Beautiful Bill Act's new 0.5% floor means for your giving.

Jim Crider, CFP®
19 min readJun 30, 2026

Asset Location

Advanced Tax Planning

Asset Location: Which Investments Belong in Which Account

Asset location can quietly add tax alpha without changing your portfolio. How to place investments across taxable, tax-deferred, and Roth accounts in 2026 — and where the rule of thumb breaks.

Jim Crider, CFP®
11 min readJun 22, 2026

Diversifying a Concentrated Stock Position

Advanced Tax Planning

Diversifying a Concentrated Stock Position: Managing Risk Without Letting Taxes Run the Show

Holding too much in one stock? How to diversify a concentrated position in 2026 — managing the tax cost without letting the tax tail wag the planning dog.

Jim Crider, CFP®
17 min readJun 18, 2026

What Is a Tax Strategist?

Advanced Tax Planning

What Is a Tax Strategist? (And How They Differ From Your CPA)

What does a tax strategist actually do — and how is that different from a CPA or tax preparer? A plain-English guide to tax strategy, who needs it, and the questions to ask before hiring one.

Jim Crider, CFP®
18 min readJun 9, 2026

QSBS Under OBBBA

Advanced Tax Planning

QSBS Under OBBBA: How the Section 1202 Exclusion Changed in 2026

OBBBA expanded the QSBS gain exclusion for stock acquired after July 4, 2025 — a tiered holding period, a $15M cap, and a $75M asset threshold. Here’s how Section 1202 works in 2026 and why the acquisition date now determines everything.

Jim Crider, CFP®
13 min readJun 4, 2026

Cost Segregation Studies

Advanced Tax Planning

Cost Segregation Studies: When Accelerated Depreciation Actually Pays Off

How cost segregation actually works with OBBBA’s 100% bonus depreciation — and when an engineering-based study earns its place in your tax plan, or doesn’t.

Jim Crider, CFP®
20 min readMay 27, 2026

OBBBA Bonus Depreciation Reset

Advanced Tax Planning

Texas Real Estate Investors and the OBBBA Bonus Depreciation Reset

How the One Big Beautiful Bill Act’s permanent 100% bonus depreciation reset changes the after-tax math for Texas rental real estate investors — cost segregation, recapture, REPS coordination, and 2026 planning watch-outs.

Jim Crider, CFP®
22 min readMay 19, 2026

Roth Conversions Under OBBBA

Advanced Tax Planning

Roth Conversion Strategies Under OBBBA: A 2026 Tax Planning Guide

OBBBA permanently extended the TCJA tax brackets but added new phaseouts and deduction limitations that change the Roth conversion math for 2026. Here's what to watch for and where the opportunities are.

Jim Crider, CFP®
22 min readMay 5, 2026

1031 Exchange Strategies

Advanced Tax Planning

1031 Exchange Strategies for Hill Country Land Owners

How Hill Country land owners can use 1031 exchanges to defer capital gains, upgrade properties, and build long-term wealth through real estate.

Jim Crider, CFP®
8 min readApr 13, 2026