The heavy lifting is in WORKING the deal, not uncovering a potential deal.

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

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. 

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).

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.

However, some challenges to consider are the additional paperwork, property inspections, and potential tenant turnover.

Hey @Beau WollensYour numbers show a massive swing in potential profit, so refining your renovation estimate is critical.

Wishing you the best in your future. 

A trip to look for a good investment or to make some contacts that can potentially be lucrative. 

But this is really your first touchpoint with potential guests who are scrolling the endless options of airbnb, vrbo, etc.