Originally Posted by camaraderie
Pops...welcome aboard! Given what you've said so far my opinion is:
Overall though, I am reluctant to tell you to go look at $60K boats given your experience and lack of certainty that you will enjoy what you now merely anticipate. For this reason I'd advise getting an older production boat in the 30ft and under $20K range until you are sure what you want and need in a boat. While the Cat 30 would be my choice in this range, there are also plenty of O'day's, Irwins, Hunter's, Beneteaus etc. that will suit you just fine as an INTERIM boat. Since the depreciation is not a big concern on these older boats, you can't lose too much on a trade-in later on and later on you'll know a lot more about what you want and don't want in YOUR ultimate bay boat.
I agree with this advice. I was in exacty the same spot as you this time last year, so I know what you are going through and think there is lot to recommend buying a cheaper boat to learn on. In addtion to just learning to sail, your first boat is going to teach you what things are important to your enjoyment on the water and you'll soon know what the "must haves" are for your "dream boat"
If had a place at the bay I would seriously look at a Sabre 28. It's a well built, salty looking boat with good performance for the bay. It has enough room for an occasional overnight, but would truly excel as a daysailer on the bay when you have the option to go home and sleep in your own bed. The Sabre 28 was my first choice for our starter boat, but the wife wanted some more room/amenities since we knew we'd be spending long weekends onboard every time we used the boat. If the end, I'm quite sure we chose the best starter boat for us and expect we'll be keeping it longer than intially expected, but If I had my own place at the bay, a Sabre 28 would be docked there.