Wow. a lot of stuff there.
Owning a house, v. owning a boat - hmm... We'll I'm in the later camp, but you have to realize that boats pretty much always depreciate, and houses (with the odd hiccup) don't. So you will need to factor in depreciation.
Then again it's unlikely you can purchase a $20K house - but you could certainly rent one for a couple of years with that... So rent for 2+ years, or buy a boat and not care if you loose it all? Yeah, I'd go with the boat.
Boat Living Costs involved
* Insurance - getting harder to get - don't sign on the dotted line until you understand you can get insurance (most Marinas require some minimum levels)
* Property tax (varies by state/county/area)
* Marina Dockage and power (a long term contract gets cheaper rates)
* That might be about it (I assume you already have a cell phone)
So you can't sail yet? No big deal. It sounds like you already know the rules of the road and how to use the VHF from your power boat days and a sailboat of that price will have a motor - so you can take your time to learn to sail. The biggest issue will be that sail boats only go slow, and at slow speeds (like at the dock) you'll find the poor maneuverability an issue (but you want to go slow so if you hit something it won't damage anything, but the dam boat won't turn if you are going slow.. Hmm). Here is a good time to use the VHF and ask the dock hands to come out in force while you are learning (of course they'll expect a tip). Also ask for an end dock (or not too far up the fairway) if you are a new boater - as this will be easier to get in and out of. Once you have a boat and a place to keep it - then you start getting lessons.
There are lots of packaged courses with nice certificates at the end of the day. I think your best bet for learning to sail will be a one on one and on YOUR boat - Hire an old salt to take you out for a weekend (2 days of sailing), and to come around before and check over the boat to make sure everything is in order - if your missing some basic stuff, you will still have time to go shopping before your 2 days of sailing practice - it is really a waste if you spend the first half a day working out where all the lines are.
Here are the things I'd expect to do
* Practice maneuvering the boat (I approach and stop just before a dock or better still a nav marker - from all directions and current/wind conditions - in forward and in reverse. Once you understand how she turns, and how fast she responds at various speeds, life will be much easier. If you can get the boat where you want it at slow speeds - docking will be much easier.
* Hoisting / reefing / Changing sails (if applicable)
* Heaving to
* Picking up a mooring ball on your own (if they have them in your area).
* And if you now feel really good - practice tacking up a narrow channel (or fairway) and possibly even docking under sail
Of course you can always join a sailing club too, or just attend classes at the local college.
I don't think there is anything wrong with your plan. I doubt very much that the boat you buy will end up being the one you want in 3-5 years time, so don't sweat about getting the "perfect" boat.
Whatever boat you get, there is bound to be some member forum you can post for tips and questions. The previous owner may well be prepared to sail with you after the purchase (if not, actually, either way, make the most of the "Sea trial").
I think the biggest issue might be the odd Hurricane - if you are working away but you need to move the boat, it can be a real hassle. Some Marinas/Yards you can sign up for haul out automatically if a named storm is heading your way - some will even move it for you - but I'd ask around and see if this is something you need / is available. Then of course you need to find somewhere to stay - the yard is unlikely to let you live aboard if a hurricane is on its way.
Gemini 105Mc - Cruising
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