I second Account Closed on this one, I feel like nothing kills a deal with a potential cash-flowing condo then a brutal HOA/Condo Association.

Are there any potential pitfalls to selling to an LLC? 

Agree with others that cold calling is your best bet.

I'm curious to know: What key factors do you prioritize when analyzing a potential real estate investment deal?

But EVERYONE is obsessed with Ohio right now and from the folks I talk to (12+/week) margins have really gotten squeezed there.Detroit still offers fantastic cash flow and is grossly overlooked in terms of potential upside.

A property manager will be your best bet.

Going to be tough to find a cash out at 80% and if you do I would be cautious about additional/potential hidden fees.

Additionally, I am aware that once I move out, I can list the home on VRBO and several other platforms to help boost bookings.The reason why I'm considering/leaning toward selling the house, is that when I begin to run the numbers, the expenses exceed what I could potentially make.

I highly recommend flying out to see the properties in person and the getting to know the city instead of picking a OOS location based on a spreadsheet numbers a turnkey company or agent shows a potential buyer or the numbers the buyer ran themselves. 

Additionally, the increase in monthly income may not outweigh the potential risks associated with taking on more debt.One potential strategy to consider is to focus on maximizing the income potential of your current properties by increasing rents and potentially leveraging any potential increases in property values.