Get on the water now.
I waited for many years for everything to be perfect, the money, the stars lined up, the kids old enough... I spent hundreds of hours dreaming in marinas, reading magazines, reading blogs and then a life changing event hit me over the head and I woke up one day and bought a "cheap" boat.
It was the best decision I've ever made.
We've since spent the last four years creating life lasting memories with my young children, daysailing, weekend cruising, vacations in the Keys and Bahamas. None of this would have happened if I kept waiting to have the money for the "dream" boat. Right now, we love this boat. I paid $6500 for it and yes, spent some time and money since then in maintenance or improvements, but that would happen on any boat.
Of course there are times I wish we had a bigger, newer boat but even if that days never comes, I can look back and smile at the time on this boat.
On top of that, the experience earned from owning a first "cheaper" boat and learning to work on it and fix it is priceless and will always be with me.
I can't tell you how much I wish I had done this earlier.
Maybe one day I too will be able to please my champagne taste.
Perhaps like with wine, before being able to appreciate a good expensive fine one, one can first learn to appreciate those is his price range
Just get out there!