Is there a clause in the contract that ties you to him after the 7 days?

Highlight nearby conveniences and any neighborhood growth to attract interest.Focus on framing the size as a bonus that buyers get more space and value for their money compared to smaller homes.

Have you looked into becoming a private money lender to put your money to work while you wait for your next purchase?

It's full of information on how to invest in other states.Look for Dave Meyers on BP.

I recommend that you learn the tax code and take ownership over your strategy.Not having some foundational knowledge and an opinion on how to approach taxes as a business owner is a huge mistake.In my experience, every single business owner who says "I just let my CPA worry about it and I focus on my business" is doing a suboptimal job at tax planning.They are likely missing out on 10s or hundreds of thousands in saved dollars every year.Stop making excuses and get to work.Just a few months of part-time learning about taxes will pay you for the rest of your career.

It specifically calls out stays of less than 7 days, though.

If you're still wanting to do it - lowest cost of entry I could think of getting yourself a list of a few thousand properties and then hammering through them for hours a day until you find someone interested. 

Welcome to BiggerPockets!

Since I live in Orlando, I pass by the villages (right off both sides of turnpike) on my way to Ocala.

Just to clarify, there is no limit to what you can raise as a nonprofit but, as Shonda mentioned, you can do a simplified filling if you intend to raise less than 50k a year.