I'm re-entering the negotiation game with the seller and explore my options with the lender now.

Or can you explore with your agent something closer to the city and find out if that much closing costs etc can be paid for?

Then over time if you are more experienced and understand how to construct a viable boots on the ground team you have faith in, then you can explore out of town stuff like you want.

It is important that you do not develop a reputation of someone who is just going to offer extreme low balls, because people talk and you want to be seen as a resource in your local market for distressed sales. 

Im exploring the idea of starting a property management company in Winter Park that helps vacation rental owners manage guests, cleanings and property maintenance - solely out of need as I am too an owner and know there isnt a reliable network up there.

Many are beginners or amateurs that can't close on the deals they are getting under contract.Make sure a wholesaler has a good track record with other investors in the area and has a good reputation with the closing attorney/title company they use.  

I'm going to meet with someone this week to explore this option.

Any reputable broker with a legit deal won't have an issue with this.

I have been exploring an auction happening in upstate New York (sullivan county) and am considering bidding on the property that is rural land.

I still have to manage the manager, but finding a provider with a good reputation takes some of the build your team challenges out of the equation.