I rented out the additional bedrooms to friends and family, charging them well below market, and sold when it was time for my wife and I to start our own adventures.

Shortly, after joining I was able to help a friend that was in sticky situation with his home and also helped another family with theirs.

A friend of mine, Ryan, who invests heavily in Baltimore, realized his interest costs were eating into his cash flow.

it is not user friendly at all.

I think you will learn a lot from it; Is This the Most Beginner-Friendly Way to Start Investing?

Your job will be to find an investor-friendly brokerage willing to teach.

This one I did 50/50 with a friend makes it way less stressful and allows me to do two projects at once without overdoing my risk tolerance. 

I’ve seen this issue in San Diego, where a friend of mine worked with a city planner to rezone a lot for duplexes and triplexes.

There may be some lenders that might be a little more "borrower friendly", but I haven't found them (nor do I have the time to look for them).You might be able get better terms if you "house hack" by getting an FHA loan, but I don't generally work with those loans.

Every Week I scan the MLS, navigating cities and towns in South Florida that are friendly (and not friendly) toward short term rentals.