Hi Keiffer,
A lot of cruisers are retired and living off of their retirement income, some are young and just living very very frugally and earning money when they can, and some save up and cruise until the money gets low then go back to work to save some more to go out again. We plan to be in the 3rd category. It will be a few years before we are ready to set out but once we do the plan is to work for 6 months at a time and try to cruise for a least a year before working some more. The actual cost to cruise depends a lot on your lifestyle (anchoring vs marinas, eating local food vs imported foods, etc) and where you go (French Polynesia and the Med are pretty expensive compared to Mexico and the Philippines).
On my blog there are some links to several blogs of people out cruising, it is a pretty diverse group.
How is The Emerald Lady? Are you doing much sailing? We had some great times on the river this summer but we haven't been sailing since the weather turned cold and rainy. We are planning to make a dodger so we can get out more in the winter (although the winds haven't been good anyway, either very calm or too stormy for our taste) but we need to make a seahood first.
Rowan
imiloa.wordpress.com