If I were you, I would run several sensitivity analysis and make sure I was comfortable with a worst case scenario.

Time sensitive...!

Also, you could consider serving him with a restraining order to your property (if able)

How to try to contact, when to contact, and what to say, so that I could get information, but not upset them any further in this very sensitive situation.  

Luckily, I have plenty of time to decide and it isn't time-sensitive. 

Last year I purchased my first piece of commercial real estate. I was very excited to start getting some monthly passive income, however long story short, the whole deal was a sham and I was left with a building gener...

I've got a couple of things that seem mostly legit- but not confident to send them my sensitive data. 

Well if he’s on the deed, he’s not “squatting” in the house, he’s a legal owner of the house with as much right to it as her absent some court order to the contrary.Having said that, if he was physically abusive to her, perhaps she could seek a restraining order (or order of protection as they’re called in some jurisdictions) which often include a move-out order when two people live together, as well a requirement to stay a certain distance away from the protected party. 

Now, I just bought my first duplex and am wanting to structure how I collect rents so that it’s tax efficient, reliable, and time sensitive.

There are things I really like about it and things that are a pain in the you-know-what, but overall it does what I want it to do (that is, interfaces with AirBNB/VRBO to automatically generate/send out unique time-sensitive codes for my guests, I can view access history and make changes via my phone pretty much in real time, and still works even if wifi is down).