I have seen the ASA classes, and having no experience at all besides a few motorboats, how realistic is it to learn to sail without killing my family and myself. Also, my wife and I have come up with several questions mostly related to upkeep and maintenance:
1.) How much do sails and rigging usually run when they need to be replaced?
Depends on how the boat is used and what care you take of them and what materials you replace them with. For instance, carbon fiber sails are very expensive and live relatively short lives—like three seasons or so. Dacron sails will be a third the price and can last 10 years, if taken care of and the boat is only sailed during the shorter northern season and normally covered to protect the sails from UV.
2.) What are the typical slip fees for a marina for a year?
Depends on the length of the boat and the marina location. Many marinas in the Buzzards Bay area are about $85-110 per foot for the season. So a 30' boat will cost between $2550-3300 for the April 1-November 1 season.
Winter storage is about $30-50 a foot out of water, more if you're storing the boat indoors. So figure $900-1500 for the winter for outdoor storage. Add shrink wrapping into the deal, and you're talking about another $600 or so.
3.) What does the yearly maintenance look like once you pull the boat out of the water?
Depends on what you're doing and who's doing the work. Bottom painting, pressure washing, winterizing the boat, and other common maintenance tasks are all within the capabilities of the average owner. Doing it takes some time but is relatively inexpensive, especially compared to having the boatyard do it at $85-100 per hour labor rates.
4.) What is better a fixed keel or swing keel for a beginner?
It depends on where you're planning on sailing the boat, whether you want a trailerable boat, which could have lower storage fees, since you could possibly store it on the trailer at home in the off-season, etc.
5.) What should I be mindful of when buying a used boat, probably will be from a marina, but how good are they usually with not selling you a moneypit?
I'd recommend you read the Boat Inspection Trip Tips
thread I started, as it will help you determine whether a boat is worth looking into further. If it is, get a survey... and make your offer contingent on sea trial and survey.
Again, if anyone is from the area and wouldn't mind helping out a newbie learn or want help with your own boat, I would definitely be up for helping to go out sailing. If anyone has anything to add, please do and thanks for taking the time to read.