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You should consider working with an accountant. That person's fees might be a bit higher than the $250 TurboTax wants to charge you, but a good accountant can help you find (legal) ways to save on your taxes.

My situation isn't as complex as yours (income from work, some investments, and a bit of money from a side gig) but what I pay my accountant each year actually saves me more.

http://opentaxsolver.sourceforge.net/

I've been using H&R Block's tax software (the "Deluxe" version, which supports investments, etc.) for years. It's not the greatest software, but it gets the job done.

How is TurboTax costing you $250? Do you need to file in multiple states?

Yep. Two states, plus investment and small business version. ¯\_(ツ)_/¯

Last year I switched to paper and pen after more than thirty years of using software.

Faster and far more pleasant. YMMV.

Use an accountant.

Ask HN: Taxes