Chris 249 said..I've spent a few weekends sailing in Sydney recently. One thing I notice is that while most boats these days are big and shiny, late in the afternoons when the huge stinkboats have gone home, one sees scruffy old production yachts of 25 feet or so heading out. Almost all of them look rough. Most are not well sailed. They seem to be used by guys about 40-50, normally sailing alone, who don't look particularly affluent.
I've got a suspicion that these guys would not have thought they could have afforded a boat a while back, but now that mooring minders are going cheap as chips they have been able to afford their dreams. They may never have sailed, but may have spent decades wishing they could. Now those boats are getting used, and their new owners (if that's what's happening) are realising their dreams. It's wonderful, if true.
I think you're on the money. 11 years ago, I was in the same situation, the bride thought boats were too expensive to buy and maintain. So I bought a reasonable Top Hat for $10k. It's probably not worth half that now, because while it's no worse than it was when we got it, it's not been improved that much either. Just maintained. So far, we've not spent more than another $13k in 10 years including insurance/mooring/slipping.
She's been from Pittwater to Lake Macquarie a few times, to Sydney a few times and whilst she's still slow, the view at the cocktail hour is the same as yours, or anyone elses.... We're on the water and that's what counts, especially if you don't have a lot of spare to splash around.