Is tax-aware investing the same thing as tax advice?
No. Tax advice is a conclusion about your return — what is deductible, what your basis is, what you owe — and that belongs to your CPA. We make portfolio decisions with the tax consequences in view and hand the detail to whoever makes the return decisions.
How much does asset location actually matter?
It depends on your mix. A household with everything in one 401(k) has nothing to locate; a household with a taxable account, a traditional IRA, and a Roth has real room. We would rather tell you the answer is small in your case than run a strategy that does not apply. No portfolio arrangement can eliminate tax or guarantee a better result.
Can tax-loss harvesting be overdone?
Yes. Harvesting lowers your cost basis, so much of what it does is defer tax rather than erase it, and the wash sale rule limits how quickly you can buy back what you sold. It is a useful tool inside a plan and a poor reason to trade on its own.
Why did I owe tax on a fund that lost money?
A mutual fund in a taxable account passes through the gains it realized internally, and it can do that in a year the fund's own price fell. Turnover and fund structure drive how much lands on your 1099, which makes it largely addressable through what you hold there.
Do I have to accept a big tax bill to diversify a low-basis position?
Not all at once. Selling across several tax years keeps each year's gain inside a bracket you chose, and appreciated shares are the most efficient thing to give to charity if you are giving anyway. If the position is employer stock from a plan, Net Unrealized Appreciation has to be checked before any rollover, because moving the shares into an IRA generally forfeits it permanently. Some tax usually gets paid; the question is how much and when.
Should municipal bonds be part of my portfolio?
Compare yields after your tax rate, not on their own. Municipal interest is generally exempt from federal income tax, which makes it worth examining at higher brackets and often not worth the lower yield at lower ones. Some issues are subject to state tax, and municipal bonds carry credit and interest rate risk like any bond.
What do you need from me to start?
Statements for every investment account, including ones we would not manage, and your last two tax returns. The returns show your bracket, your carryforward losses, and which thresholds you are already near. Without them the work is guesswork.