So along with the non-paying tenant, the property management company adds its own chaotic and confusing element with their shaky communication skills.

Reminds me of a home we had in Australia where the inside had an in-ground pool but open to the elements, it was gorgeous & all the bedrooms opened to it.

An Annual Permit: In Monroe County an owner or agent is required to obtain an annual special vacation rental permit from the Planning & Environmental Resources Department for each dwelling unit prior to renting any dwelling unit as a vacation rental unless an exemption to the vacation rental permit has been issued for the property as provided in Section 134-1(b) of the Monroe County Code.Initial Special Vacation Rental Permit Application Fee: $490.This application and fee is for initial applications only, not renewals.Renewal of Special Vacation Rental Application Fee: $100.This application and fee is for renewals only.NOTE: A special vacation rental permit is nontransferable between owners.

One element of a legal contract is both sides have to give "consideration" which is typically money but as @Tim Swierczek mentioned, it could be your goat or it could be a service you are providing.

With furnished units the design is key - and if you've done a good job of keeping your "permanent" elements versatile and as timeless as possible, then you can change out the decor here and there to suit.

In cases like this; I have found that it's all about finding the situation you and all other involved parties are comfortable with from a livability standpoint - while still offering ample upside as an investment.Don't get me wrong; when you bring the personal/emotional element into the purchase decision it definitely makes getting deals to pencil out more challenging. 

I would also pull the elements every 1-2-3 years  (start at 1 and then judge how bad they are before fixing on a schedule)  A tankless water heater will require acidic flushing At Least every year.  

Keys elements to put on your checklist when hunting for a property are:1) Separate utilities for each unit.  

Thanks @Owen SchwaegerleGreatly appreciate the reply, as this is a multifamily couldn't I get a break on survey, environmental report, possibly transfer same insurance into place etc...Is it even possible to negotiate a loan assumption or am I stretching? 

For some mixed use properties, you need to get an environmental report, similar to the standard that is used when you buy a commercial property.