All that money from visitor spending and taxes will just dry up and blow away. 

I have worked in investment banking, private debt, commercial banking, and private equity all at “prestigious” firms and closed $30bn+ worth of deals.

Private money lender will give the same terms on either property, so financing is not a player. 

I'm an investor and private/hard money lending consultant in the Evansville area.

You want to spend $65K and do tons of work, headache, hassle and sleepless nights to end up with $10K in equity?

It has been more difficult than I thought to find a lender because in the area I live in I really don't need a loan larger than what I could spend on a single family home.

You're looking at spending a minimum of $350k, but likely well over $400k.

And also how much of my time do I have to spend managing/worrying about the place.Have you ever done deals like this?

During my spare time, I enjoy crossfit, reading, cooking, and spending as much time as possible with my wife and kids. 

It gets cumbersome, to say the least and I now appreciate more what some back office staff can do when focused on something like this.Anyways, under mint you can create categories for your spending so it's just a regular occurance to go into the platform and categorize your expenditures.Another option is to open a business account on a per property basis.