You have a lot of questions- I'll tackle the first one.
Question 1) Should I form an LLC and/or S Corp for my 1099 job? Or what should I do?
Answer: Firstly check with your contractor/employer since it might not allow payment to an LLC or S Corp. If allowed, then an LLC with an S Corp election (IRS form 2553) is probably the best way to proceed in that it will likely help save on self-employment taxes. However with the benefit comes more paperwork such as filing an S Corp tax return-Form 1120s and all required employment tax returns since under S Corp rules you will be required to take a fair market W2 salary from the S Corp.
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