We weren't boaters when we bought our boat. We vacationed on it twice for a couple of weeks at a time before retiring and moving aboard full time. So starting with little knowledge is not that big of a problem.
Heck - you can buy and sail a 50' boat with no license and no training, and the difference in insurance for having had some classes is pretty minimal. So the actuaries don't think it is that hard either.
Most people do come from boating as a hobby, but we met lots who never did any boating until they retired onto a boat. Some of them have sailed to some pretty distant ports.
A $10,000 boat is going to be pretty tired. But Skylark mentioned spending another $10,000 on upgrades. By the time you do that, you can have a pretty servicable boat. Ugly perhaps, but servicable.
Maintenance is a fact of life, but the vast majority of maintenance is usually done while you are aboard, if the boat is your home. Even when the bottom is being painted, you'll see boaters living in sailboats sitting on dry land with supports holding them upright. The only time we ever moved off the boat for maintenance was when we refinishd the teak parquet floors, and we knew we wouldn't be able to keep our dog (and his hair) off the wet finish. But we painted the entire outside, did lots of engine repairs, plumbing repairs and upgrades, electrical upgrades, and so forth, all while living aboard.
One nice thing is that boaters are generous with their time and knowledge. More than once we had other boaters, either total strangers or casual acquaintenances, help with repairs that we weren't sure how to make.
Hurricanes are not the threat they might seem. You'll see the east coast boaters (like us) head north to Norfolk and beyond by May or so, both for cooler climate and to avoid hurricanes. Hurricanes are only a factor that far north every 20 years or so.
(Many insurance policies give better rates if you are at least that far north from June 1 onward.)
Of course that every 20 years sometimes means THIS year. When Hurricane Isabel hit the mid-Atlantic area last September, we knew weeks ahead of time that it was likely to come our way, so a week before it was due, we and hundreds of other boats went up rivers to spots where there were no open stretches of water that would allow waves to build up. Most people got off their boats and stayed in a motel, but many stayed with their boats.
Of those who took these steps, I did not hear of anyone with more damage than minor paint damage caused by debris in the water rubbing against the hull.
All these boats that head north will hangout in the Chesapeake until the end of hurricane season, around mid-October give or take a few weeks, and then head south for the warmer weather in Florida.
That trip south is no big deal for novices. There are lots of boats going the same way, so you follow the pack to a great extent. Staying out of shallow water is not much more than staying between the bouys. Most novices and seasoned boaters alike will wait until there is a group of boats and an excellent weather forecast before crossing large bodies of open water, as when they go to the Bahamas (a long day's trip).
You asked about missing the conveniences of land. Space and good internet connections are all we missed. The internet problem is just about solved in most places. Lack of space - well, you just have to learn to deal with it.
I'd say most full time cruisers don't have cars. They and the other boaters will quickly learn places to stop where access to shopping is easy. This information is widely shared. The more popular places are those with easy access. Beaufort NC, for example, has a maritime museum that makes available for free an old station wagon to any visiting sailor who wants to take it for an hour for a grocery run. North Myrtle Beach SC has a shuttle bus ($1) that takes you to area shops. Vero Beach FL has an extensive free (donations welcomed) bus service going anywhere you could think of. Miami Beach has a large modern grocery store that you can reach by water. And so forth.
Getting a car to where the boat is located when the boat is moving every few days or even every few weeks is completely impractical. When we had to have a car, we used one of the car rental companies that would come out to where we could meet them.
You'll notice I underlined "cruisers". These are the vagabonds who usually won't remain in any one place more than a week or two. There are also lots of full time boaters who will stay in one location essentially all the time. This is the case in a lot of places where a boat will be at a dock and the owners will be living aboard. (That dock typically adds $2500 a year to the cost of living.) There are fewer, but still quite a few, places where the boats are at anchor in one spot year around. St. Augustine and Marathon FL are two places that come to mind. There are also boaters who will spend winters in one spot in the south, and summers in one spot up north.
In these cases, where the boat is in one place either all the time or for many months at a time, you'll find that a lot of the boaters have cars.
Dory36
