One of my best friends thinks I'm rich and while I may have more than she does, I she was earning more than me for a lot longer (I make more than her now) but she spent her money on $6K vacations. 

The best way to find an investor friendly broker is at a RE meetup, but you can also just ask around in your local network or google.

 I can't count how many times my friends have called to ask what to do about their leaky ice dispenser.

Recoup those expenses, my friend.

I have a rule , never do business with family or friends .

But there is no black and white guidance that I could find.And, in conclusion...1st conclusion: no FICA until the child's 18th birthday.2nd conclusion: tax law is muddy (I would add two capital letters, but it's a family-friendly forum)3rd conclusion: pay your CPA, we have to deal with it daily, and it takes skill

So, it's either get your real estate license or have a really good friend who will list them for you who wants to look them up (but most agents don't know what they are doing and do it wrong).

If you haven't already connected with an investor-friendly lender yet I'd highly suggest that.

Are you trying to hand your “friend” a 50% taxable gain that you’re going to keep?

Mid-term is more likely to work in any market than STR, but I think you would be surprised at how well an STR could do if there are no other options like that in the area (think people's parents or friends coming in for the week(end)).I've seen a lot of people grimacing at the net-negative house hack (it's just a product of rates and low inventory in a lot of markets) and this is one option to try to recoup some of that loss.