A young investor with just 1-2 properties, 3 years into their journey could potentially be a great partner for friends and family.

The IRS has challenged simultaneous "drop and swaps," so allowing some time between these steps is advisable.You hit this right on the head with your answer with TIC.You could also potentially do a Exchange Post Distribution (Swap and Drop).

But, for future reference, in Ohio there is a little used approach to always get your money back.

Most STR markets have seasonality, and there are untold issues in the future that will effect cashflow. 

If that furniture grants you that performance potential go for it.It appears you're looking more so for what your break even point is.

If I, as a bond investor, am uncertain about what the future will bring, I might just sit on the sidelines and not invest.

In the event that you don’t have money to build a cash buyer’s list first by using bandit signs or pulling lists and contacting potential cash buyers, you have two other options:Option 1: Attend local real estate meetups and or your local REIA meetings.

It also offers a chance to shift into something more passive, reducing the hands-on management that seems to be more of a hassle now that you’ve moved.That said, the rental income potential from your properties is worth noting, but there’s a limit to how much you can boost your cash flow, especially after already making significant upgrades.

He's helping me to narrow down a potential multi-family property that I will be house hacking, (the deadline I have given myself to be in it is May).

Fannie Mae will allow you to transfer the deed to an LLC if you decide to try to go the conventional route, but the loan would still be in your names and you'll need to pay a title company a second time post-closing to do this  for you. 3) I can't speak for the area so no comment there4) If you're self managing, make sure you find vendors you can trust in the area since you won't be able to easily verify if an HVAC guy, plumber, etc. is trying to rip you off and tell you to buy something you don't actually need. 5) Make sure you have clear alignment of goals and a clear operating agreement that spells out what to do if those goals start to not align in the future since you'll be jointly obligated to these properties.