Or did you tackle this project with just research and how-to videos under your belt?

I don't even ask our tenants to change the filters since sometimes getting the metal pieces of the furnace back together takes a little mechanical talent and when the filter is inside the furnace there are a few bad things that occur e.g. if the door is not properly closed the safety switch will be open and the furnace will not operate and you get to pay a technician to solve the problem and tenants sometimes don't installs filters correctly and the filters get sucked up into the blower squirrel cage.

The Midwest and sun belt seems to be a good fit.

You need to get some reviews under your belt and that will help generate more bookings.Have you checked the other places nightly rates compared to yours?

Instead I have a few properties under my belt that generate me income every year.

Buy properties in the rust belt where growth is happening and property is still cheap but appreciating.

Good to get the first one under your belt early : )  I am going to take a slightly different approach than Nathan, not that I think he is wrong but to give you options. 

My boyfriend and I are investors in the GR area, as we get more deals under our belt (when it makes sense) we will probabbly hire a property manager.

Of course those thoughts r in my head but so is the thought that I finally can get something under my belt.

Once you do all that, you will have your first property under your belt, keep educating and financially preparing and in no time you will be ready to purchase another, but this time you will know what to do from there :)