Personally, I'd cash-out refinance into a 30 or 15 year loan.

If he has a $5MM loan in place, what was that used for / is it coming due/ was it short term/ etc.?

The members here on BP that talk about STR auto-run systems didn't install those systems and find dependable cleaners & handymen overnight.

Assuming since you did any FHA loan, this was a househack?

I will always look at the air handler and make sure tenants are installing fresh filters (most neglect this item).  

Since it was over 12 months with my HML, I ended up taking the property under my name with a 30-year conventional loan.

.🔹 Creative Financing – Traditional loans don’t always work for distressed properties.

Any good resources for learning about hard money loans?

Instead of a traditional down payment, I would give them some money (maybe just to bring the loan back to even).The upside if taken over the loan at the current balance, with some rehab and hopefully getting the front lot back would be a nice ROI. 

This is a large community and someone might give you some insights on the lender or the loan officer.