* Currently sole proprietor. Will switch to LLC or C Corp in 2018 (depending on income), but I'd talk to your accountant to find out what's best for you.
* I'm remote currently with high utilization client (as a subcontractor) and smaller retainer clients.
* I am a firm of 1.
* I have an accountant to manage taxes and finances. I keep meticulous records of what is a business vs a personal expense. The subcontractor gig is insured by the main contracting company. The retainer gigs stipulate it is knowledge/access only, so without any IP deliverables required, so there's no need for insurance on that. I may get insurance if my employment situation changes in terms of the contracts I take on. For this, I'd talk with your lawyer.
* I would just buy health insurance through the state. I live in MA, so we have to have something. We're both young and healthy, and she has an incredibly stable job, so I don't worry about this one too much.
I should point out that I'm very new to this (4 months in) so definitely don't look at me as a source of having "done things right" - I am learning every day and still sweating it all.