Sole Proprietorship Tax Resources?

I didn't see any obvious wiki links, but apologies if I just missed them. I am trying to estimate my taxes for 2020 and keep stalling with questions.

Does anyone have recommendations for good online resources or advice books, so people can learn how to do this themselves? I called some CPAs but I am very hesitant to pay $200/hr (seems like this could easily cost me over 600 bucks just for tax planning).

I can't figure out if my health insurance premiums factor into my AGI or are simply a deduction? Alternatively, maybe that's a stupid question cause those are the same thing? Do I have to know now for my estimated tax payments if I'm going to contribute to a traditional or Roth IRA? I keep becoming overwhelmed about what it is I don't know, so any sources that would give me a broader understanding of US tax law (specifically for self employed individuals), before I try to fill out a 1040-ES again, would be great.

submitted by /u/thesavvydog

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