@Stephen LynchI’m involved in this in my market for OOS REI and I find that it’s where your thread ended that matters the most - having someone who is an independent party verify all work performed.

I assume even though the problem on our side was taken care of, the other sides owner is deceased and has been a roach party of free food and open fornication. 1.

Hey Joe,  The more conservative the lender the more likely they are to stipulate these items-I'd guess this is a bank loan.  

Be EXTRA conservative with your numbers.

FYI, Tenant A could be on the hook for your legal expenses and lost rent since they were the responsible party. 

Unless you are only using it to have the tenants pay a 3rd party. 

and I spoke with the bank earlier today and confirmed that we should qualify for a jumbo loan that would allow us to make this work out.The place I am getting stuck is trying to figure out any kind of realistic estimates for whether the three cabins are actually able to generate enough positive cashflow to allow us to eventually step back from our jobs and/or running the numbers for everything in a way that I would feel confident enough to try commit to something like this.Would it make better sense to try and start out with something more simple/conservative?

I am more conservative and analyze at 8%. or 1 turnover per year.

The advantage is that you can pay it back whenever you want within the 5 years and the interest goes back to your own retirement not some 3rd party lender.

If this is someone you have worked with before or someone you trust and have confidence in then you should form a legal partnership including a partnership agreement that clearly conveys what each of you is responsible for and how you will each be held accountable and the penalties in the event that one party is not doing whats expected of them.