Where to start, what to buy.
Here's the deal. I'm a 60 year old wannabe sailor who has just enough experience to know how very much I don't know about the sport. I'm a novice. (I've sailed Flying Scots and a few small - 27' to 32' - cruisers, none of my own). My wife and I recently moved to the Annapolis area and I would like to buy a boat. My spouse supports me on this, but she does have some reservations.
My goals are to 1) gain enough experience so that I would be comfortable chartering a boat on vacations. 2) gain this experience by sailing around the Chesapeake on weekend trips. 3) eventually, when I retire in a couple of years, do some coastal crusing, say to Florida on the ICW.
I'm 6' 3", 200 lbs and in reasonably good shape, and reasonably athletic. My spouse is 5' 4" and 100 lbs. and she will admit to not being athletic at all. So, whatever we get, it will have to be pretty simple to sail since I will probably do most of the work. (This is where her reservations come in. She's not sure that she could handle many of the tasks expected of a crew member. )
A big question that I have is whether I should start with something around 27' and then, after I've got the experience and am ready to retire and go on longer cruises, buy a larger boat, say around 35 feet. Or should I start with the larger boat (with more room to make the spouse happy). The brokers that I've talked to almost unanimously advise me to go for the bigger boat at the outset, but I'm not so sure. The 'intro to sailing books' often advise one to get something smaller, usually because one can get a better boat for the same money, expenses are less, and smaller boats get sailed more frequently.
Finally, as I noted, I'm 6' 3" and bunk length is an important consideration.
I'm only considering used boats and am prepared to spend up to $50K (for the larger boat, $30K for the 27 footer). [I just did a search on Yachtworld and found 138 boats in the Mid-Atlantic Region, 27' to 36', priced up to $50K.]
What are your opinions - on where to start (27' or 35"), and on what boats to consider? Also, do you think it would help ease my wife's concerns if we signed up for some lessons as a couple?