HC- logic would say to get a small boat or charter
until you have some experience and know exactly what you want in a boat. Sometimes logic doesn't prevail, and the heart takes over. Which is fine. Often, owning a sailboat isn't logical or economical. That said, the Catalina
is a fine choice. Decent resale value, decent quality, and decent sailing. $35k seems a bit high to me for a Catalina 25... and I understand that the one you're considering is almost new. If you went for the 25', you should be able to pick up a good used one for about half that.... and sell it for about the same later. The price
on the 28' seems a bit high... but it may be a better value in the long run.
It's easier to learn to sail on a smaller boat. But you also need to enjoy being at anchor
or at dock
. If you intend for day sailing
... a 25'er might suit you better. If you intend on a lot of overnighters and week-long sailing... you may want the 28'er. I don't mean to suggest that a Catalina 25 isn't good for overnighters or week cruises... the Cat 25 was our first sailboat (we learned to sail on it), and we enjoyed several years of weekends and week-long cruises on it.... all very fond memories.
Please consider that your first boat will be just that. As you gain more experiences in sailing and cruising, you'll find what you want in your next boat. So, I'd consider both boats with that in mind... along with depreciation and resale.
Best of luck, and welcome to sailing.