He was initially terrified of buying a place with a pool.. thought it would scare off insurers and sink his returns.

They're not just going to sit on it and wait, can't afford to. 

You deduct what you can from the deposit and charge them for the remainder.If it takes longer and the deposit won't cover the losses, send a bill to your departing tenant and give them 30 days to pay.

And congrats on owning three paid off rentals!

Thank you so much for the information and advice!

Quote from @Michael Daley: This is why I'm thinking more about taking the STR route until I can refi with a better interest rate. 2 units (2/1) in a good area at $1.3 with some ability to update and has a garage or ADU capability would work if we can get $5000 per month for each unit.$10k STR rent on $1.3m property at 80% LTV  will be negative cash flow when properly allocating for all the expenses.  

@Doug Bontragerfind a good property manager and get their opinion

The killer for us and why we did not look at any leased land cabin is the no renters.  

I've sent you a connection request to learn more about your journey as I'm looking to do a similar venture. 

Then I would reach out to a couple PM’s and ask them how much rent they would charge, their fees, and what you would net.