Owner shouldn't care about your DTI.

It could be for a family member, or a young renter who doesn't care much about cooking, or an AirBNB guest.Or, if push comes to shove, 2-4 unit Fannie/Freddie financing exists -- and this could be the push for originators to actually start paying attention to that market.

Take care of the hard job first.  

Most sellers only care if you close so you can usually use another form of capital stack other than what is on the agreement, however, the seller can force you to use the originally agreed-upon payment method. 

You can wind up with title issues if you are not careful. 

Foundation issues are very very real there and can really destroy returns if not careful.  

- Any tips for staying updated on regulation changes?

It's a fairly unregulated space (charging grandma $750 to puts around for 3 hours, after moving the old box from the horizontal sensor, which was the only problem with the garage door to begin with), so some combination of carefully reading reviews (you have to actually read them to make sure it's not 200 fake reviews), and maybe not giving them the full contract all at once, is in order. 

One thing to be careful with though is that if you go the personal loan route, you need to ensure your DTI is still fine and you will still qualify for your VA loan assumption AND the second mortgage.

So I want to be careful to not stretch her too thin.