Hello Zac.I don't know how real estate closings are done in Massachusetts.I can tell you that in my state of Illinois, a buyer does not have to hire an attorney but then he will have to trust that the Seller is complying with the terms of the contract. 

Assuming your tenant hasn't read it either, this is where you need to educate them and inform them that you will be complying with the lease terms.

It's guaranteed as long as they comply with the program. 

In the future, I recommend no more than one verbal warning, then a written warning with a clear description of the penalty for failing to comply, then penalize or evict.

I make my LO's for 3 to 5 years to give the person time to qualify and sometimes they never exercise the option, move to another state (life changes) and I sell it on Lease Option again.Just make sure the Lease is one agreement and the option is a different agreement to comply with Dodd-Frank which is simple enough to do.

Also, if you have to do major rehab to a place where the renovations exceed 50% of the current market value, a lot of cities will require to bring up the property to current code, which can add to your expenses to repair things you otherwise would not, such as making the place comply with energy code requirements and next thing you know you gotta replace the windows and insulation. 

I've complied a list of hard money lenders, through recommendations by fellow lenders, agents and BP forums.

Co-insurances is between 80-100% requirement usually with a 10-20% penalty in the event of a failure to comply.  

The document processor should be able to to the agent "We received some tax returns, but they did not comply with the instructions, so we are not going to mark them as received.

Also, make sure your lease is either drafted or approved by an attorney to make sure you comply with all local tenant-landlord laws; otherwise, an experienced tenant will find loopholes to exploit.