If you want to delve into the investing world, based on what you've shared- this is critical. 

So the timeline is critical.

That's going to be a critical piece for you.

Please do not come here to criticize my landlording skills.

The maps and things are possibly not as critical at first, but they will tell you if there are things like utility easements or (maybe) flood zones that you need to think about. 

So having the deed under your LLC name is the critical step. 

Does anyone have a better process or have any constructive criticism for mine?   

The typical realtor is more experienced with retail buyers who are looking for homes to live in and will know good locations to buy or a good price on a property, however won't know as much about rental rates, vacancy rates, etc. which is critical when you are running your ROI analysis of potential investment properties.

Second question, Should I go toward the top of my budget (qualified at $260,000 and currently looking at properties near that amount) at the start, or should I scale back and do a smaller property a little further away to test the waters and gain some experience with finding and managing tenants, but will allow me to easily afford the mortgage in the event of vacancy.Any advice, or criticism, would be greatly appreciated.

Location is critical for STR, you will get more bookings if your property is located to where the travelers go.