Re: Champagne taste on a beer budget
As an apartment dwelling, non-land owning citizen a trailer sailor is a less then ideal setup. Throw in the Mini-Cooper and it is just a bad idea.
I'm with the chorus here. Get out there now on a boat you can afford and like AND one that is suited to the Chessy. Deep keeled boats are less than ideal for the Bay. I'd suggest you look at some of the keel/center board designs that are out there. They include the boat I have: Tartan 27', draft 3'6" with board up, 6' with board down. There are a few other similar keel/center board boats out there to look into as well. You should be able to find a boat similar to a T27 for well under your budget that is just a notch or two below the Nor'sea you seem to like (nice boat BTW - about the only boat I'd consider moving up to from my T27 since I really don't need 'more' boat but a better boat is something else (I can't afford right now)).
The problems that occur when people try to sell their old boat is that they often leave a list of obvious items to be fixed/maintained un-done. Boats that look like crap to you will not look good to a prospective buyer. In the used boat market the mantra has become: "It is not about the make or brand but the maintenance and upkeep of the boat." A poorly maintained boat is not going to be the first to sell.
I also like your short list of boats. PSC rates quite high.
"The cure for anything is salt water~ sweat, tears, or the sea." ~Isak Denesen
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