My dad owns a local painting/drywall company, and has expressed willingness to borrow against his house's equity to help me get my first deal.To add context, myself and my dad are not going about this as if he's "doing me a solid".

Also, other people who provide advice have their own followed words, so try to use common expressions in your post, at least once. 

Hi BP,It's been more than a year since I posted an intro and expressed interest in starting my REI journey.

Perhaps some of the college-debt soaked millennials have gotten over being terrified of home ownership and are finally deciding they might want to buy a house after all, and the Govt wants to buy their vot.... errr...I mean, find a way to help them achieve the American Dream!

I've expressed my interest in getting a multi family house, or renting a room above a garage etc.We're currently living in Southeast CT, but are looking to move a bit closer towards Hartford, but not too close.

A primary reason the majority of Americans are in financial distress is the myth that buying is always better than renting.

Would The ASHI American Society ir Home Inspector be a good place to start?

Unless your friend has already expressed interest in loaning you money, I wouldn't go that route, you would be pressuring a supposed friend to do something they really wouldn't want to do otherwise.

@Chad Pore I have 5 SFH all insured through American Family.

I'm not an attorney, and what I am expressing here is from my personal experience and knowledge.