However, saying that there are many companies that do both that are amazing and don't do things like this, so I'm not suggesting that doing both is inherently negative. 

I typically don't suggest anything in the reunion area for investors because of the restrictions around what management companies you can use and what amenities your guests get access to.

Being out of state, I would suggest vetting your "team", meaning find an investor realtor, lender/s (hard $ / long term), property manager, contractors, etc.

Anyone have any suggestion for me?

Any advice or suggestions would be greatly appreciated.Thanks in advance!

Where I differ with most of the posters on this thread is that I feel solutions can be developed to address the problems and something similar to what the OP suggests would be viable. 

Isn't it like you're suggesting somebody to do something (investing in Costa Rica instead of the US) while you (the experienced investor in Costa Rica) does the exact opposite with your own money?

Suggestions on learning more about contract for deed?

Do you have any suggestions on how to go about this?

Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).