I win in court and tenant is kicked out in 24-48 hours.In 90% of all situations, the tenant leaves before I have to file in court, I use their deposit to cover unpaid rent and as much cleaning/repairs as possible, and I move on.

Regular property managers for single houses and condos may not be willing to take them.I don't want to self manage either.Do the tenants have a higher rate of default than condos and single homes?

Installment Payments: The buyer makes regular payments to the seller, which include both principal and interest.

If the one document you got showed a deposit of $1700, then that is what she's owed (minus any cleaning costs or damage that occurred after you bought it (ie you know she did it). 

Any one of these could and regularly trigger a special assessment.

Are you buying in an association that will provide cleaning services?

I want to avoid holding costs with him holding onto it while we renovate, but how to I make this as clean as possible?

You can potentially qualify for a regular rate & term refinance of the 91k loan (plus closing costs) within 12 months.  

I just occasionally check the notes and pictures from the clean. 

Better tenant selection and regular inspections will stop this from happening.