Yes I spent a few hours and I have to make a few trips to the city dump(Doesn't cost anything and its a 2 minute drive) but the tenant is difficult and I wouldn't be surprised if he made a big deal about it and wanted to take me to court over it. 

Can the tenant request their entire deposit back and force me to pursue action through small claims court?

Go to court and file for eviction. 

Will the city of Cleveland provide lists via the courts for homes which have had water lines shut off?  

Make sure you are comparing more than monthly fees as some PM's include Eviction expenses (paperwork, court appearances, etc.) into their guarantees. 

Does anyone know of any Connecticut meetups near the Windsor area at all?

A higher court would quickly overturn such a foolish decision on appeal. 

I found out that you can no longer see evictions or eviction proceedings in the NYC court website anymore. 

Your hangup is because you don't understand it and therefore you don't know HOW to present it. 1 or 3 page contracts are great...until you end up in court.

Maybe you need an advocate they know, like is surely the case in zoning court.