§ Strategy Guide
BOCA RATON · UPDATED MAY 2026
Investment Strategies
We're not investment advisors — we're tax preparers. But after-tax investment returns are what actually matter, and most investors leave significant tax efficiency on the table. These are the tax-aware investing moves that show up in every high-net-worth planning conversation.
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Asset location: which account holds what
The same dollar invested in a tax-deferred 401(k) versus a taxable brokerage can produce very different after-tax returns. The general rule: put high-tax-drag assets (REITs, actively traded funds, taxable bonds) in tax-deferred accounts, and put low-tax-drag assets (broad-market index funds, municipal bonds, qualified dividend stocks) in taxable accounts.
Tax-loss harvesting
Proactively selling positions that are down to realize losses, then reinvesting in a similar-but-not-identical security. The realized loss offsets capital gains; up to $3,000 of excess loss offsets ordinary income. Automated at some brokerages, but often poorly done — beware of the wash-sale rule (30 days either side of the loss sale).
Dividends: qualified vs. ordinary
Qualified dividends are taxed at long-term capital gains rates (0/15/20%); ordinary dividends are taxed at your marginal rate. To qualify, you must hold the stock through a specific window around the ex-dividend date. Most US-stock index funds produce nearly all qualified dividends; REITs almost never do.
Municipal bonds for high earners
Interest on municipal bonds is generally federal tax-free and, for in-state bonds, state tax-free. Florida residents don't benefit from the state-tax exemption (Florida has no state income tax), but the federal exemption still matters for high-bracket filers comparing taxable vs. municipal yield.
Section 1031 for real estate investors
Selling appreciated investment real estate creates a large capital gains event — but a Section 1031 "like-kind exchange" can defer the entire tax bill by rolling the gain into a replacement property. Strict timing rules: 45 days to identify, 180 days to close. Plan before you list.
Florida residency + capital gains
Florida's lack of state income tax means capital gains realized while domiciled in Florida avoid state tax entirely. Investors who recently relocated from high-tax states should time large gain realizations carefully — and document the domicile change properly.
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