I've heard Guesty for Pro has been having so many issues lately and for the price it's not worth it.

It is a business, so run it like one, as @Tom S. said, start the process and follow through.Unfortunately you're in a Blue state so this will be more difficult for you, so yes get a lawyer if they don't respond immediately to your 'pay or quit' notice.Don't take any more partial payments, that will delay your case!

The numbers work, but there are so many easements on the property.

I am managing and maintaining 10 units currently and have been for a little over a year so I am starting to get a feel for things.

Single family homes are great assets but starting out I'd try buying a 2-4 plex  so you get a feel of what real estate investing is all about.

I don't know the entire situation so I say can be reasonable.

There are good areas for rentals in pockets all over town so don't think of this like a big city where you might have to narrow down your area to one suburb or specific area of town.

My new business is still cash starved but I’m making it fine so might be safer leaving the funds there  - I don’t know where trailers tap out.

@Michael Baum also hit one of the most important things - dynamic photography that changes with the seasons and mixes itself up so it's not a stagnant listing.There is no hack to be the best at something (just look at all of the number one bestsellers on Amazon who sell 100 books total), just work on the product, the amenities, the dynamic pricing, and be resilient and responsive to feedback from the first guest on.

I am concerned about theft during and after renovation so a policy that can cover that would be of utmost importance.