Home mortgage is $3700/month and $500/month extra payment towards the principal.

I just wondered if working with one of these mentor groups would add an extra layer of expertise, or if it wasn't worth the hassle.

100% financing, no payments, financing in extra "cash out" money upfront so you can do a rate/term refi once you pay them off... 

They like extra room to avoid accidents, etc....Just my $0.02....

Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).

They're pretty organized, but expect annual inspections and some extra paperwork. 

That way you wouldn't need an extra policy.

Before you close, can the rent from your buddy and the midterm tenant cover your mortgage, taxes, insurance, plus a bit extra?

You'll want to have an insurance agent familiar with rentals since a lot of the extras on your coverage that you will want, the average insurance agent won't know to give you. 

Using a family address could expose you to unnecessary risks in the event of any legal or financial issues related to the business.Additionally, these virtual offices often provide extra services like mail and package handling, telephone answering services, and access to meeting rooms, making them a more professional and practical solution.