Almost anyone can afford a luxury car. 

You want to make sure they can afford to rent your place.

As a professional, you can't afford to mess up and cross legal issues, be very careful who you get advice from especially at REI meetings.

How much are other people paying for health insurance, that is not provided by ones spouses job or job?

Additionally, while a precipitous fall in oil prices has had a negative impact on “oil patch” locations, it has effectively increased the spending power of the American consumer.While there are still concerns regarding the overall health of the economy, the current real estate lending environment remains active and strong as a whole.

This is not something I can afford to do at any point in the near future.That I'm aware, there isn't a local real estate investors club or meet-up group where I can talk to others who invest locally - so I'm a bit stuck for advice here.Ultimately, I'd like to get my foot in the door in this business as soon as possible, but the financial barriers to entry seem almost insurmountable here in the Cayman Islands.

Health care?

As soon as you can afford it you need to hire Team members to help you.  

Wix.com is an easy to use interface and or workpress through godaddy etc are very affordable, but not as easily customized.

Denison and Sherman are both pretty good secondary markets that are affordable with decent schools.