Talk to your insurance agent and be sure you're covered.

If this is not available then we have done demo and just removed the structure.Sidenote for people who see the title: Do not burn down a house on purpose for insurance reasons.....That is called fraud and is criminal :) 

You need to think about not just the potential income but also the potential problems such as city ordinances, state law, insurance, potential eviction issues, etc.

Insurance.

I've been running into some trouble/challenges when it comes to being comfortable talking to sellers i.e. on initial/introductory/cold calls and sometimes in appointments/meetingswhat are some tips you guys may have o...

I know taxes and insurance have gone up a lot in that time so I understand that problem but the solid rent increases in that time have been able to cover most of that (at least for me it has worked out).

Its also a good idea to build relationships with realtors, contractors, insurance agents, real estate attorneys, and property managers in your area so take advantage of events, conferences, and meetups.

Mainstream homeowner policies won't cover sober living because they don't account for the risk of multiple people recovering in the same home

What if you are currently house hacking, with a homeowner's policy.

That strategy is not going to work at all. 99 percent of agents don't even know or understand seller financing and will just think it's a scam (which it is most times these calls come in since the caller has no money and therefore is irrelevant to a regular homeowner).