However, a lot of concerns can be mitigated with looking at their past rental behavior in a lot of different settings.

Originally posted by @Marie Pruden:Thank you, Ricardo P. and David To for your kind concern advice. 

Condos are cheaper than houses, and to my mind, a vacationer wouldn't care much about staying in a bigger place for their short stay, and would be more concerned with a good location and a nice view.Thoughts?

The best banks that I have found based on your main concerns are smaller, regional, community sized banks.

Unit 3 - mid-term rental (this would be best for the most private unit as most mid-term renters are more concerned with privacy and creature comforts than amenities)4.

The problem (as you have cited) is trying to understand what you need (you don't know what you don't know), where to get it, qualifying its source(s), and the validity and usefulness of all that.Pardon me if I've gone into this too much, but I meet many people with the same concerns that you are voicing and this is offered, as much as possible in direct response to your post.Please feel free to contact me if you have any comments or questions. 

Then tell us the nature of your remaining questions and concerns as to each remaining aspect, so people can have intelligent, focused, SHORT, conversations with you on each issue you present. 

It could certainly be a concern - but depends on a lot of factors - are you looking multi or SFR? 

The concern with places like Irvington will be once you move out and no longer owner occupy how do you raise rents legally.   

I could care less what happens to the prior homeowner or if they go after him, as far as I am concerned.