Cashflow may not be immediate but if you run your #s, you'll be able to see how long it'll take to cashflow and what kind of equity you can expect to build within your first few years of house-hacking.I began househacking in 2010 while working an NYC job (Health + Hospitals Corp., formerly HHC) earning a base salary and overtime pay that are nearly identical to what you posted here.

I kind of gave up on Stessa, just do not have the time to deal with ongoing computer issues and constantly not being able to communicate with a company.

Feeling uncomfortable with sellers stems from some kind of fear. 

I'm looking at working with insurance companies/temporary housing for my next rental, I have an LLC, but I don't know what kind of credibility they look for since I only have my personal residence that I house hack.

You have to look at rents per sales price in both areas and see what kind of return you can get versus what you are getting now outside of real estate.

What kind of lease do you have in place?

We have started looking into wholesaling and subletting but still kind of overwhelmed about the amount of information we still don't know.

Maybe I missed it, Bill B kind of eluded it but why not do seller financing? 

Of course then covid pushed rates even lower, which of course because no one wanted to borrow money with that kind of uncertainty.   

That kind of experience builds confidence and reduces risk over time.