My boats were a little more costly than Nancy's case. Completely aside from the cost of the boat itself - I spent $8-10K/yr on launch/haulout, moorings, storage, maintenance/replacements, sails, insurance AND $15-20K/yr when I was racing! And I was a small fry, the "big boys" spend orders of magnitude more. Over 20-30 years, that adds up to a pile of money - and frankly that's what drove me out.
I definitely miss owning a boat after being an owner for almost 25 years, but I can't justify the ongoing $$$.
Let me make the case for spending a fair amount of money on a sailboat now.
If you buy a good used boat, let's say for $75K to $100K, for a 8 to 15 year old vessel, the depreciation is pretty much wrung out of it, meaning you could buy it, change your mind 5 years from now to go bigger or smaller or just different, and you can pretty much get your money back out, providing you bought something nice like a Sabre, Morris, J Boat, Alerion, Island Packet, Tartan, or one of the many high quality European brands, or what ever you define as upper level or of higher quality. So, you have tied up some money, which doesn't make anything in right now in CDs or money market funds, but you will get most if not all back when you sell it, so it's really not costing you anything, except what you might have made on it in another investment, no sure thing and possibly you could lose some of that money too. Sure, you have the anxiety of selling your boat to buy the next one, like I'm going through right now with the 2010 Alerion Express 33 I have on the market, but that's just part of changing sailboats, a little like changing colleges where not all of your course credits transfer.
If you buy a new boat, and again, if you choose wisely, you're likely to keep it for a long time. You're a relatively young man and you'll be sailing for at least another 25 years, providing you look after yours and your lady's health. In that scenario, you could make the case for spending $200K+ on a 2013 "All singing, all dancing" fully featured boat of your choice, using the equity in your present boat as the down payment and financing the rest over 15-20 years. I think you can still write off the interest on the basis of it being a second home.
How much you can afford for a new sailboat is absolutely none of anyone's business but yours but if it were me, a certified lunatic who has owned 70 cars, 8 sailboats thus far, 6 motorhomes and 6 motorcycles, but still have the original wife of almost 50 years, I would do it. As one of my old bosses, an Englishman by the name of Ware, said to my saintly wife who was protesting my decision vehemently to buy a new boat back in 2004, and was looking for some persuasive help from him, when I was moving from a perfectly good four year old Colgate 26 to a new Alerion Express 28 costing three times as much, "Nancy, we are dead a long time. Let him have his boat."
In other words, if you are gainfully employed and have most of your other bets and obligations covered, buy something very nice, a new fully equipped boat or a used high quality sailboat, because we are indeed "dead for a long time."
Nancy Anne Sailing Charters