I have sold a couple of businesses as well, and speaking from experience, you are never more vulnerable to make a mistake than when you are sitting on a giant pile of cash.Also, I agree with @Corey Conklin - I'm a big fan of "overflow cities/towns" in the sun belt.

One of our favorite discoveries is that IT'S TRUE, dream opportunities DO land in your lap, the longer you're in business! 

I don't really need to know much else about someone - if they can't pass this test, why should I believe that they will be able to run a business that will generate cash?

Some go out of business.

I am glad to be doing business with his company.

Network in person, see if they have a publication where you can post your deals and what you are looking for, and if there is a larger annual conference for investors locally consider getting a vendor table to talk about your business and what you are looking for.

You’re running a business not a charity after all. 

I've learned that it's extremely important to find balance in this industry as your passion for your business can impact your personal life greatly!

Quote from @Griffin Malcolm: Open an LLC and apply for a small business line of credit from Key Bank.

We exclusively travel during non-peak seasons, so we would be looking to rent out completely during busy/peak seasons, and would stay at the place during slow seasonsQuestions for the experts out there:1. which development(s) tends to be the best for ROI/have the best occupancy rates?