Everyone things bigger and better is easier and that is not always the case.

Which is the better situation for the long term?

If you do you will get better terms. 

To explain the situation a bit better the 3rd party company is called Obligo, according to them once they receive the repair estimate from the management company they instantly pay them.

A better arrangement would be, paying him an acquisition fee, a property management fee and then splitting profits pari-pasu to your capital contributions.

SCREEN better.

The owner will have to clean up and board it up.Even better, I like the idea to buy it!

I'm still doing market research and can't decide what would be a less riskier option for me, is it better to find a property in a vacation destination that's more rural and outdoors or a property in a more urban/metro area?

You would be better off purchasing deals from a wholesaler in your area.

I wish I had a better update guys, but it's been an absolute nightmare of an experience.