Sounds like you want him out now and money motivates a lot of people.Make it contingent on the condo being in good condition and professionally cleaned so that the expectation is set before handing him over any money.

I get that these places have an old school style, but can't you recreate that with modern clean looking materials. 

All I will need to do is some clean up and and paint.

We will assist with things that may be endemic to the property - i.e. filling a hole in a foundation to keep out mice - but our lease clearly states it is the responsibility of the tenant to keep the place clean and pest free.

They will call a lot but will keep things clean and let you know wasap.

With short-term rentals, you are responsible for those things but also things like pool care, lawn care, pest control, electrical, cable, furniture maintenance, dishes/towels/utensils/etc, cleanings, (you see where i'm going with this), essentially you are operating a hotel. 

The people whom work there know which contractors are relible and clean etc.

When I discovered heaping piles of bat guano in an attic of one my houses, I rolled up my sleeves and cleaned it all out myself.

Covering all bills, cleaning, maintenance, etc.

While there was a benefit, which is a clean bank account per property, as all the transaction of property ABC was in bank account ABC, the above hassle factors were bigger than the benefit, at least to me.In general, as long as the assets are not huge, most of us, if not all, agree that putting one property per LLC (regular LLC or series LLC) is an overkill.