By way of background I am currently in the NYC area but have family out in Orange County that I visit frequently so thought it was worth a deeper dive into the market.

I know a lot of people focus on Short Term Rentals over when you get closer to the water, but you need to be careful about what city you're in as STR are a very touchy subject.

It offers a few other ideas like the following: The Conventional 97 loan:Loan size may not exceed $510,400, even if the home is in a high-cost market.The subject property must be a single-unit dwelling.

If you sell the property under two years you're subject to a higher tax rate in Colombia, 33% from memory, as opposed to the standard 10% capital gains rate.

If I have the cash I can invest it and realize a greater amount of the benefits of real estate but if I do it with the SDIRA I think I would be missing out on a couple things such as depreciation and be subject to UBIT.

As far as money and structures goes,  look at strategies using Options, Master leases,and Subject to purchases which can all be used will little cash if done properly.  

If you're interested in learning about this space, you may want to start out with a few books on the subject.

I'd just get a lot of advice on the subject. 

As Brandon frequently suggests, I was trying to analyze a bunch of deals to get used to the process and getting to know my local market.

If your tenants are not interested in purchasing the property, you can just list the property and state you are selling it subject to the lease.