I am willing to offer cash for keys as a last resort but I'd rather get them out by advising them that this will be a costly decision on their behalf and that moving out would be the best option for them.

This gives me a maintenance/CapEx cushion from the outset, if there’s a break down or emergency.Second, the property seems poorly managed.

If you could only base your investment decision in one single item then it should be location.

Carefully review and understand the specific process and approval criteria or standards the governmental org. will use as a basis to make a decision on your request. 

A response that you would hear from a person who has no aspirations, like "Poor Dad".

You have to either be willing to make sacrifices or else make a decision to  just stay in the "comfort" zone.As an investor with a portfolio of 20+ properties it is worth it.

The answers to "will the current owner continue to depreciate it" and such like are not in my wheelhouse, and are probably part of the reason the owner is reluctant to make a decision...

Do NOT buy in a community where you do not get to VOTE on major decisions.

If they have been paying their rent, and there aren't any expenses related to poor upkeep of the home on the tenants part, then I wouldn't be too worried.  

Most investors use LLCs for an entity but to really decide you should probably talk to both an attorney and CPA.You have not included a lot of information that would be relevant to the decision: - Do you have a net worth large enough that you are a target, so need an entity?