Looking for a recommendation of a contractor who can secure the property, change the locks and do winterization.

If you buy a 2nd position you are buying subject to the senior lien; If that lien is in default then the total payoff ( if in default or foreclosure, interest, late fee's, foreclosure fee's, etc. ) is still owed and secured on the home. 

Mason,I would serve the three day notice for rent, or whatever is required by your state laws, and once that has expired, file for eviction proceedings.

What I will love to do is some fix & flips instead of that to start securing those large funds for my REI, unfortunately I'm a poor college student haha.

We'll likely be going to small claims court.What I'm specifically wondering about is the security deposit. 

This eliminates the need for the claimant to formally file a lawsuit to trigger insurance coverage. 

How do you collect the security deposit and the first month's (and last month's) rent?

In MA, you cannot rent to a family with children under the age of 6 if you don't have a lead certificate on file, which means it's been tested by a lead inspector and made safe by a licensed deleader.

I had the same type of experience with another contractor and was thinking about going after him in court but decided not to because he had an Corporation and I was afraid he would file bankruptcy if i went after him.

Are you enforcing late fees, notices, and filing for eviction?