..... A friend of ours belongs to one of the clubs in the San Francisco Bay area.. He bought a NEW 42 foot Hunter and turned it over to the sailing club.. they paid the payments, kept it serviced, and kept it clean.. in five years he has a boat at no cost to him, except a monthly membership payment, which is less than a slip fee..
Now I'm sure that a new 42 foot Hunter is the boat for everyone, but you don't bitch very much when the boat is free..
I never knew that this option existed. If I was in my 30's, 40's, or 50's and knew that it did exist I think I might seriously consider it.
I'd still like to possibly have a separate boat, but you can find 17-20 something trailered boats for less than $1500 that are in good enough condition to day sail. The OP doesn't have a driveway, but lots of people do. So you have your little cheap boat that you can peck away modifing and using on a moments notice if you want for not much of an outlay. Then you also have all those other boat options that you talked about and a nice boat 5 years down the road. Then sell the little one or if you are like us keep it. Nice plan!!
With both of us hovering around 70 at some point driving 2200 miles to our larger boat and taking it out will be too much for us, but we will still have our other boat to enjoy past that time and will enjoy it between trips to the larger one now. So we are engaged somewhat in what I described above, but we are paying for both
. I like your option,
Our 37 Endeavour --- Our 26 MacGregor --- Trips With Both