I take photos of every surface in every room, prior to move-in, plus close-ups of things that might not be obvious in a larger picture (insides of cabinets, appliances, closets, tile, etc.).

I do see some multifamily property come up to the market  surface.

Moreover, you can be sued for any reason, especially if you have rental property, and if you have plenty of insurance, the costs of defending yourself shouldn't come out of pocket.That is kind of a down and dirty that just scratched the surface, but to answer your question, I personally would go with a variation of option 3.

Obviously fewer repairs are better, but none of this sounds hyper unrealistic on the surface, @PJ Kolnik.  

We've been approached by potential clients in the past where something didn't "feel right" and with a little targeted Google searching we've been able to surface what exactly wasn't "right."  

@Shawn Blackwell Define overnight guests for her in your fashion.

I agree on the doubt of getting a variance on this, your best bet would be to connect them in some fashion so it can be converted or be looked upon as a single family. 

Of course I have several agents that I have met "the old fashioned way" but many more who I have connected with through instagram, some which led to doing literally millions of dollars of deals together.

I'm one of the case studies in the House Hacking Strategy that BP published.On the surface because of the lack of income and savings, I don't think Seller financing will work.

Call me old fashioned, but I do like the ability to sit down with them in person if needed :)