I know there's a lot of threads here like this, and I apologize in advance if I'm walking a frequently-trod trail with this line of questioning. I have read quite a bit, and have tried the search here, but it's hard to find posts relevant to my particular train of thought since the search terms are pretty common and not exclusive to what I'm looking for input on.
In a nutshell, I'm looking for advice on a plan for the next 5 years which culminates in owning and sailing a "real" cruising sailboat.
I live in corpus christi, tx. It would be an understatement to say we're blessed with sailing weather. My experience is a couple dozen afternoons in trailer-sailers, a childhood/youth full of commercial fishing in Alaska and a single 28-day passage from tahiti to hawaii on a 50-ft wooden gaff cutter. The good news is I am well aware of the realities of passage-making and ocean weather. Bad news is, my wife is not. She is very much "on board" with the ideal of cruising (exotic ports of call, blue lagoons, etc...), but other than a couple sails on a 20-footer, she's a true greenhorn.
So the goal in the next 5 years is to spend as much time sailing and developing skills as we can, to familiarize and comfort-ize my wife with all things nautical, and to save money and (near the end at least) buy and outfit a cruising boat.
I see a few different general paths, all with pros and cons. I would LOVE some input from the more experienced crew on the relative merits of each way.
1. Get a dinghy sailer, spend a lot of time sailing it. Pros: cheap, easy to store, low cost of ownership (equalling more money saved). Cons: small, wet, probably not enough boat for corpus christi bay on many days out of the year. Wife factor: small enough not to be intimidating, but wet, probably not too comfortable, no head, a one-trick pony (only for sailing).
2. get a trailer-sailer/pocket cruiser, spend a lot of time sailing it. Pros: Still relatively cheap, more comfortable, can camp with it, better in stiffer wind than a dinghy. Cons: A step up in cost of ownership, more hassle stepping mast before each outing, still days where wind will be too much around here. Wife factor: Drier, more confidence-inspiring. Note: we had a gulf coast 20 a couple years ago, hence my username. We only got to take it out twice before circumstances and a move forced us to sell it. Stepping the mast was a huge hassle, and probably stopped us for taking it out more than we did. I'm sure there's easier ways to accomplish the mast-raising, and I could probably work on that aspect, but it definitely left a mark.
3. get a cheap pocket-cruiser and keep at the marina. Pros: Quickest dock-to-sail time of the bunch, should be able to handle most days in corpus christi bay, head, bed, etc. Cons: with dockage, most expensive to own and buy, draft probably make it tough to camp with Wife factor: confidence-inspiring, maybe indimidating
4. Go through the ASA classes and bareboat. Pros: Real education in sailing on big boats by professionals. Cons: as expensive (for both of us) as purchase of a nice used boat, less overall water time. Bareboating very expensive.
5. An option I haven't considered?
I'm all ears folks, thanks for any input, and again I'm sorry if this has already been covered in depth at another point in time.