Champagne taste on a beer budget
I have $10,000 saved for a first sailboat for weekend sailing on the Chesapeake. Ideally, I'd like to bump it up to a budget of $15,000 next spring plus a contribution from my spouse for first-year expenses.
My problem (part of my problem) is that my tastes tend toward small cruisers that are out of my budget. I could describe what I like, but it might be more telling to list the boats I like: the Bristol Channel Cutter, the Nor'sea 27, the Pacific Seacraft Orion, Dana, & Flicka, the Shannon 28. In any decent condition, most of those would send me 2-to-6 times out of my budget.
My specific question is - is it better to just get out on the water in a decent boat within my means, or should I wait a few more years to try and save up enough for what I really like? Part of me just really wants to get out on the water, the other part of me knows that whatever boat I get with my $15,000 will eat up any savings that could be going to the dream boat.*
*This is the other part of my problem - I'm not the worlds greatest saver. Those rules for retirement accounts that don't allow you to touch that money without severe penalty were built for people like me - I'm great at putting money away, just also really good at pulling it out again.