Is this legal? 

Essentially, you are paying for something you hope you never have to use....but if it does happen, you have multiple parties in your corner fighting off a claim, for many years if needs be, and even if the limits of one were exhausted, you have another...and the legal fees alone could be large, so nice to have the insurers footing that bill and having an interested in settling or disposing of the suit....great question, though, could you be overinsured?

So if the contract states is not assignable, but that section is crossed out and written atop is "this contract is assignable..." will that hold up if a legal battle is pursued?

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.