He plans to do more with me and bigger pockets (no pun intended) if the deal goes well.

Mid-term rental and BRRRR strategies are definitely solid approaches to start with.

I would listen to a podcast I did with housing economist Jay Parsons.

My Mom's family grew up with two generations of the local family get togethers and knowing all the extended cousins, so did my wife's family.

I cannot think of a way that you (the LL who stands to "benefit" by them repairing their own space that they are paying you to use) will come across in a positive way.Plus, the tenant who incurred damage due to the other tenant's leak, may have some legal rights to have the tenant with the leaking pipes pay for the repair in both spaces.Now, beyond the legal side, you also need cognizant that most mom and pop tenants (which I assume these are) are not great with their money.  

Most off market purchases cannot easily be comped with mls properties that comparatively have no risk and are in much better condition).so …Pay for a fixed fee mls listing with the property already under contract.  

How cool would it be with a little bit of searching and probing if you could buy Microsoft or Chase at 80 cents on the dollar? 

Do not just buy LVP with underlayment already glued on it as a layer.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Of course I did that.... before even posting on Bigger Pockets, but I'm not seeing anything specifically about this company, just a bunch of businesses with similar names that do construction.