I’ve met most of my partners through in-person events because it’s easier to get a feel for someone’s personality and long-term vision.

You have a freelance job and you can qualify as REP I sharing this from my personal experience.

I haven't seen a lot of discussion about this topic which surprises me since I feel like personal finance people talk about HSAs all the time! 

I think they just started offering it again.Dyches Boddiford has a good course https://assets101.com/events/hard-money-lending-online/I and several others have taken it.

I bet you were floored when the person ordered every package you had to offer!!

Do you rely more on the deal itself or the person behind it?

And you can't legally dictate how much they carry for personal belongings. 

If the LLC is the maker on the note, there's a good chance you'll be required to personally guarantee the note.

When you say "we," are you speaking about your business or your personal tax returns, or does your business flow into your personal returns because you file as a sole proprietor?  

Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness.