Being dependent on the kindness of strangers is no way to go thru life.

Bro Investor makes too many promises, pays way too much, and relies solely on the advice of strangers on the Internet to win that first deal.

Is it challenging to find people willing to live with strangers?  

The best advice I can give if you really want to invest and create financial freedom is to forget the advice you get from strangers on the internet.

I know I don't want to be questioned by the FBI at all, but at least if it was for what I did then whatever, if it's for a stranger I don't think so.

Is it a roommate type situation where everything is shared with strangers?

Before you pay for a sub-to course, try cold-calling 500 people and ask them to sell you their house, but they have to keep the mortgage in their name and trust you to pay for it, while you let a stranger live in their house, and you'll close them out in 2 years.That is the essence on the "buying" side of Sub-To. 

You just joined and the year just started, so perfect timing for that.When I started I decided that I want to develop a portfolio of residential real estate investment that generate cash flow for me, my family but also the next generation, i.e. my daughter.If I were in your situation right now, especially because you said that "Skills like raising capital, sourcing/closing deals and underwriting/analysis are no stranger to me", I would probably focus on being the bank for people who want to own their own house/residence in markets that have a good ratio of price and rent level.