I guess I must be very fortunate indeed. I've been saving for years, purchased the boat I wanted, which obviously beat the Hell out of the checking account and I have marketable skills that I can take with me.
In my case, I've been a freelance, outdoor writer for nearly 40 years, sold thousands of magazine and newspaper articles, and sold loads of photos to go with those articles. So, on every trip I record notes on my digital voice recorder, shoot lots of photos of nearly everything, then upon my return I query some of my editors to sell them articles.
Unfortunately, the print media business is rapidly falling apart, and most of the stuff you see on the internet is donated by those who wish to see their name in an article. Consequently, the freelance writing market is quickly coming to an untimely demise. Therefore, I must make do with my only, other marketable skill.
For the past 30 years I've also been an entertainer, a one-man-band singer/musician. I perform regularly at high-end restaurants, bars, retirement communities and private parties. This will be my primary source for generating an income during my upcoming, 7-month voyage down the ICW to the Florida Keys, then over to the Bahamas.
I already have a couple jobs lined up in the keys where I believe I'll be able to do some horse-trading in the form of a couple nights of performing in exchange for a week of slip rent with electricity and water. If this works out OK, I'll use it at other locations as well.
The main problem associated with this is transporting my equipment. I have lots of room for it on the boat, but once I arrive at the dock then I have to make arrangements to transport it to the bar or restaurant. Now, if the job is a marina Tiki Bar, transportation is not a problem. But if the job is situated a fair distance from the boat, I may have to either rent a car or call a taxi-cab, both of which can be expensive.
The other problem is you cannot be anchored or on a mooring ball and bring the equipment to shore on a dinghy. It would be quite foolhardy to expose $7,000 in music equipment to some nut case in a jet ski or go-fast boat's wake.
Hope to see some of you in the sunny south next November,