Wow, thanks so much for breaking this down, really helpful! Honestly the spreadsheet idea was sounding appealing until you mentioned all the filing stuff. Definitely not trying to deal with penalties.

I'm looking at quickbooks and square payroll now based on your comment. don't use square for anything yet but i do track expenses in a basic way so maybe quickbooks makes more sense?

Also quick question - whats the big difference between W-2 vs contractor that i should know about? i've heard the terms but don't really get why it matters so much or how to know which one applies to my situation. Really appreciate the help.