u/revel911

I'm about to move an automated equities strategy from paper trading to live, and I'd like to get the tax side sorted before the first real-dollar trade, not after a surprise 1099-B. I've read the basics and will be talking to a CPA, but I'd like to hear how people actually handle this in practice.

Setup: Long-only U.S. equities/ETFs, event-driven, holding periods from a few hours to about a week. Nearly all gains will be short-term. The strategy also re-enters many of the same tickers regularly, so wash sales seem inevitable.

A few questions for those already running live:

IRA vs taxable: Are you trading in a Roth/traditional IRA or a taxable account? If IRA, how do you deal with contribution limits when scaling capital? Any brokers support API trading in IRAs reliably?
Trader Tax Status / §475(f): Did you elect it? What made you comfortable that you qualified? Was eliminating wash-sale issues worth it?
Wash sales: If you're trading in a taxable account without §475, how much of a headache are they really? Any software or workflows you'd recommend?
LLC / S-corp: Worth it, or mostly overhead at smaller account sizes?
Estimated taxes: How do you handle quarterly payments? Do you automatically set aside a percentage of gains?

For context, I'm starting with a mid-five-figure account and will scale if the strategy proves itself. Mainly trying to separate what's worth doing from day one versus what only makes sense once account size grows.

Would especially appreciate any "I wish I'd done X sooner" advice.

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High-turnover trader, all short-term gains: How are you handling the tax drag?