As for the land, with some looking around and a possible off market deal, with time I’m confident I could find an R2 lot for relatively cheap compared to the build.

Protect yourself with that criteria If you are in a stable market and are confident your house will rent soon, maybe now is the time you will consider whether you are going to accept felons and the rules around that.

Bartending is the only place where I can make $30-50 an hour at the moment.Luckily I do share this house with my sisters and their husbands, so if an FHA purchase and living in a house for a couple years is the only way, I may be able to swing that.I'm fairly handy and have done many of my own repairs to this house over the years, so I'm fairly confident in my ability to be able to handle a slight fixer upper. 

I am confident in that market.I am okay with the challenge of it being harder to manage a few different units at the same time - and I would be on-site at least for a year.Investigating the market is simply a time and money aspect.

That is not trueAlso How confident are you it’s a good deal?

All other metrics equal- I have much more confidence in a +$1,000/month cash flow projection (or even a relative metric like +10%/year) on a $750,000 house than I do with a $300,000 condo.

Hello,How do you build the self-confidence to approach a property owner about buying their property?

So, here goes my advice:[Since you already have confidence in the sponsor and know their work, you have made the due diligence easier.]

@Taz Zettergren to be honest, I too like the Little Rock suburbs more than the B-ham area.I have been more active though in Bham because I really found a great team of agent/PM/Lender in that area and I feel confident in their ability to get me a good deal.Unfortunately, I cannot seem to find an agent/broker in the LR area that gives me that same vibe. 

I am confident that one or two will stand out in meeting your particular needs or will feel very comfortable to you.