Currently situated in San Diego and can only afford rent for now because house prices in SoCal are bonkers.

We believe it’s not the buyer’s fault if title issues arise, and it wouldn’t be right to keep the earnest money in those situations.

Not sure your living situation but something I would definitely consider if possible. 

I feel like I've dealt with every time crazy situation there is here in Chicago with squatters, evictions, drug dealers, etc., and I still love Cook County because I have a solid team and underwrite deals properly.I think @Paul De Luca nailed it on the head, though - it seems like you are quite risk-adverse, so maybe given your risk tolerance, it's not the best idea, but if it were me, I would not think twice about it, and find a rock start property manager who knows exactly how to vet tenants.

This was the kind of situation where most people would turn around and walk away, but not us.

Unique situation that I’d like advice on.

Normally, we would say no and wait until the end of the lease but due to the situation and hardships we would inspect for pets and pet damages.

Regarding the condo/townhome situation in Fort Myers vs Bonita Springs, I would say the more important things to focus on would be the association fees charged, what is included in those, and the rental restrictions of the association.

I would just add that probate isn't really a painful process in most situations.

I have a situation where a person I know is moving out of the country and would be looking to put their home for sale in the summer.