There are a couple of approaches I would suggest you can choose from. 1.

We prefer 2bedroom 1.5 bath.We also want to invest here in KY.A few perks about my guy, he works for a builder, investor.

The commercial real estate market (which includes multifamily) has suffered a big hit over the last couple of years. 

Hello Emily,  Its definitely nerve racking purchasing your 1st property, a couple things to consider.1.

Most of the time - and especially since Orlando area bookings have cratered - we don't have back-to-back guests outside of the holidays, so in practice we usually just provide the info to the guest a couple of hours early.

I prefer my method because with the $800/month estimate you might buy a property believing its a great deal, BUT sell it after several years having made negative cash-flow.

Look those up and see which you prefer. 

Really looking for a couple best places to find expired listings.  

I just want enough stable revenue to pay yearly expenses, hire a property management team, and pay the debt preferably in 5-10 years.

That means either a duplex or such where you live in one apartment and rent out the other, or get a couple of roommates.