If our analysis shows that we can cash flow the property we'll make an offer to take it off his hands, spend $ to improve, and then cashflow it.  

It doesn't have to be a 2nd job with a few helpful tools in place.

Better to get a job quote than an hourly wage.

But I'm fine to put down 20% on total value (80% LTV), I have a full time job, so I can support my underwriting with the steady income. 

You can directly contribute to improving the area, helping residents access safer and better-quality living conditions.Hopefully, this gives you another avenue for real estate investment in a growing market like Charlotte.

I've been watching YT videos about what to do when you don't get enough inquiries via FF...I'm still finishing up some improvements at my place so I haven't listed it yet.I've asked a family member who is an RE attorney (but does not have experience with STR/MTRs) to look over my lease.

I recommend that you learn the tax code and take ownership over your strategy.Not having some foundational knowledge and an opinion on how to approach taxes as a business owner is a huge mistake.In my experience, every single business owner who says "I just let my CPA worry about it and I focus on my business" is doing a suboptimal job at tax planning.They are likely missing out on 10s or hundreds of thousands in saved dollars every year.Stop making excuses and get to work.Just a few months of part-time learning about taxes will pay you for the rest of your career.

I always tell clients my job is not only to help guide you and help find something, but know how to get OUT of a deal if a cancellation makes sense. 

You are paying them to do a job, I would let them do it and hold them accountable.

 I bought my first house in 1987 and  5 years later I got a job transfer from Miami to Central Florida.