I have seen bk last 2+years, all the time cost legal fees (if you have atty), but earning interest at the same time.

We plan to be honest and set clear boundaries.As far as the 'eviction' goes, everyone is on a month to month agreement so we'll give the proper and legal 30 days notice. 

An eviction is a legal action following a lease violation.

Usually "after I do a walkthrough" would be part of that speech, but not in this case.At least in our area, getting the keys back is very helpful from a legal standpoint (clearly shows tenant has given up possession).  

If you want read a real eye-opening book about being a landlord in Massachusetts, read "Legal Tactics: Tenants Rights in Massachusetts" by Annette R.

Before I start searching for my first deal I want to make sure my wholesale contract is in line so that I can avoid legal trouble.

There are different types of fees: legal, late, dues, ... sometimes they may be more prone to wave some type of fees but not others. 

If the lease has terminated you can move to eviction but you must provide the proper legal notice in order to get a court date (probably a full 30 days).

Is this legal?

If all is good, I pay the money for the credit history and legal history background check.