In the last 10 years we've signed 1500 leases and only had two evictions- those two evictions took between 4-6 weeks from start to finish. 

Looking for new lease templates.

Scrub their PM agreement, lease agreement, etc.

He says it's in good condition, could use AC and a heater, maybe some new siding but otherwise in good condition.He has a renter there paying $1600 month to month who wants to stay but has no long term lease. 

A Quad is still better due to the fact that you have 4 leases and 4 rents coming in and still can get a conventional loan. 

LTR or Mid-Term RentalIf STR doesn’t work out, consider mid-term rentals targeting professionals, which could offer higher rents and more stability than long-term leases.3.

Then there are other items that are negotiable in terms of marketing to get the place rented or at time of signing lease between the two parties.

My long-term tenant wants out of his lease due to his adult son passing away.

One option: You could seller finance your house to someone or lease option.

We started doing bi annual inspections of the properties asking with 6 month leases so we could go in and keep an eye on our property. 6 month lease don't work for section 8 but we were able to inspect.