Ultimately we decided that the cost of doing the cost segregations right now was not beneficial enough since he didn't really have any reason to pay for them and if I would have covered the full cost then the benefit wouldn't have been significant enough to me.That said, I do know there are ways to structure your operating agreement where the depreciation can be distributed to different partners in different ways.

Was that with Smart Home Choice by any chance?

It is a good group of like minded investors and I think the value you would gain there would be very beneficial as you get started. 

When i signed up, I couldn't find any reviews on BP and I hope this helps people make the right choice.1. they make it sound like they do a lot more work than they actually do.

The PS will send it back to him unchanged and he'll have no choice but signing it this time.

This way, Tenant A gets a little financial "help" beyond their actual expenses and for Tenant B, it's a total choice to take advantage of a W/D or not.

Your worst-case scenario (not specific to MA) would be having to sue to get them out as a holdover, but this is really reserved for worst-choice scenarios when owners choose the first renter or don't do any due diligence.

Tell her she has two choices: move out or face the judge.

We were both pretty lucky and made some smart choices with what we had.

If so, I'd 1) join a real estate investing mastermind that focuses on your asset class of choice (multifamily, industrial, storage, etc.) and learn as much as I could - it's worth the $10k-$20k in both knowledge and connections.