A nearby lot suggests the land could be used for a multifamily home for student housing, but based on the area (and due to the nature of students) it seems that each rental unit would not go for much money, and even if it did cashflow, I have seen videos of landlords (and know from experience) that housing students can be destructive and costly.But, if I could figure out a purpose for this land which would net the owner a profit over the long run and gain enough knowledge to sell the idea, I would buy the lot with the purpose of flipping it to a developer who is more interested in long-term gains.

This will give you an indication of the conservative nature of the cash flows at the property.

As time has gone on, I assumed that both properties would be easy to rent as I would target other officers living in those areas who’s BAH would naturally cover my mortgage.  

However- given the nature of this question, I am going to assume you have no experience as a landlord at all.

I don't really ask them as a question --- I just naturally try to bring it up during a conversation to see what he or she has to say.       1.

If you start keeping your own counsel, it becomes more natural over time.

@Jay Hinrichs - Yes, I am talking about lots with gradient big enough to make a basement with the natural slope.

Due to the bank financing and overall nature of the deal, I'm thinking this is more of a HELOC property than cash-out refinance.I'm getting caught up in calculating my usable equity after the rehab is complete and my property value increases.

I have an old buddy that sells for a developer out there and I’ve been in contact with him as of late, so naturally he is optimistic about the area but I want to make sure I'm doing the proper research.

Im sure given the nature of COVID right now, its hard to get random people to live with each other - thus not a lot of room rentals in the area