Agents and lenders I've spoken with have mentioned the possibility of a 203K loan, but my understanding is that they are a huge PITA and slow. 

I'm sure insurance specialists on BP will chime in with helpful information.I'd recommend seeking another opinion from an insurance agent who can list and explain coverage options. 

If you have different individuals then you need to make sure that there is an equitable way to share the three benefits of owning real estate: 1) equity, 2) cashflow, 3) tax write offs. 

@Don Konipol we solved it by learning from the Intentional Living Community (the OG's of independent adults living together). 

In the future, I would love to start with owning multi-family rentals and eventually get into investing in high density rental developments.

Unless you're on the beach, i'd avoid the flip flops and board shorts, but Also I think most people get defenisve or put off by suits when they are knocking on someones door, so Business Casual, collard shirt if that is something you'd wear or a Clean- Non Graphic T (unless you had your own made), clean cut dark denim jeans -- and some clean shoes. 

This is not complicated folks, what happens as affordability to OWN your home decreases?

"Long Distance Real Estate Investing" by David Greene is a good options and will help with getting an idea of good markets all over the place, not just your own backyard. 

or should I file a claim with my own landlord ./ homeowners insurance?

Who owns the home, you or the boys?