I think there are a lot of good boats in the 20 to 25K range. I agree that many of the early fiberglass boats were quite heavy without being especially sturdy. The 1970''s was in some ways the sorst period because boats were getting lighter but engineering had not improved. By the 1980''s there was a better materials and methods as well as a better understanding of designing fiberglass structures.
Probably my favorite is the Tartan 30 from the 1970''s. These are nicely designed and reasonably constructed boats. I have posted this list before but here is my list of favorites under 25 K.
-Albin Ballad (30 feet (1973-1978) $12-20K)
These are reasonably fast and very well built and finished boats. They are not especially roomy but are good boats for short handing. They are beautiful looking boats. Most have a Volvo 10 hp diesel.
Albin Cumulus (28 feet-(early 1980''s) $15-18K)
These fractional rigged sloops would be a ideal first boat. They are reasonably fast and easy to handle. They are nicely finished and typically have diesels. The interiors on these boats are not exactly plush but is reasonable.
Alberg 30: slow, wet but rugged and cheap to buy.
Beneteau First 30 or 30E (30 feet (early 1980''s) $18-22K)
Fairly modern design that should sail reasonably well. Not the most solid boats but fine for Florida and the Bahamas. They had diesels and pretty good hardware. The 30E might be a fractional
rig, I don''t recall.
-C&C Corvette (31 feet (1967- 1970) $15-22K) and -C&C Redwing (30 footer ( 1965-1970) $12K- 20K)
Attractive and reasonably venerable designs; they are not especially fast but OK for the era. The Corvettes are moderately long keel/ centerboard boats and so are great for poking around the shallower areas of the Bay. The Redwings are fin keel/spade rudder boats and in many ways are less suitable for what you want to so than the Corvette.
Cal 2-30 and Cal 2-29''s (just under 30 feet (mid 1960-early 1970''s) $10-18K)
These are reasonably built racer cruisers that have reasonable accommodations and pretty fair sailing ability. Like the Cal 25, the design is a dated and if the gear has not been updated will be less convenient than a more modern design But these boats have gone a lot of places.
Dehler 31 (31 feet (Mid to late 1980''s) under $20K to mid-20K range)
These are really neat little boats. They are reasonably fast and look easy to sail and single-hand. They are fractional rigged and have a very nice interior plan. They would one of my favorites on this list.
Dufour 2800 (28 feet (mid 1980''s) mid $20K)
These are OK boats with a big following. They are not my favorite but they would not be a bad boat if the price were right.
Irwin Competition 30 (30 feet(mid 1970''s) $12-16K)
These were well rounded little boats that sailed well and had reasonably nice interiors. There was one that dominated its class in PHRF for years. Irwin''s were not the most solidly built boats and so you are looking for a well maintained example in reasonably good shape. You may have some serious beefing up to do if you plan to do the Carribean.
MG27 (27 foot (Mid 1980''s) under $20K)
Nice little fractional rigged English boats. They seem to be well mannered and have an interior layout similar to my now sold Laser 28. They have a diesel aux. But tiny tanks that will need to get upgraded.
1970''s vintage Tartan 30''s, (30 feet( 1970''s) under $20K)
These are my favorite masthead sloops of that era. They are good all around boats. Most still atomic 4''s but you can find them with diesels.
Late 70''s/ early 80''s Hunter 30''s, (30feet (15-20K)
These are very under appreciated boats. We have had two in my family and again it is a matter of finding one that has been upgraded and is in good clean shape. My Dad raced his in PHRF and went for a couple years without finishing lower than a first or second. They are roomy and surprisingly fast.
70''s vintage Pearson 30''s (Not Flyers)
These are very venerable racer/cruisers. Of course they come in all kinds of condition from really well maintained and up graded with good racing hardware and a diesel engine to stripped and trashed. You can buy them from under $10K (but you would not want any in that price range) to something approaching $20K. You should find good boats in the high teens.
Pearson Vanguard, Triton, Wanderer and Coaster: Pretty classic old boats from the 1960''s. They were simple, heavily built and pretty cheap to buy. They are a mixed bag in that their original hardware is bound to be dated and pretty worn out. They are slow, wet and don''t have the most comfortable motions in a chop, but lots of these boats have gone to far away places. Again you really want one that has been maintained and upgraded.
Ranger 29 (29 (early 1970''s) 10-18K)
These are good sailing and nice cruising little boats. They were not the best built boats and so you should be looking for a clean and updated version. Still they offer a lot of bang for the buck.
Wylie 28 and Wylie 30 (28 and 30 respectively(late 1970''s to early 1980''s) 10-15K) These are neat little boats that sail well and are really pretty interesting. The few that I have seen have good hardware and have had simple but workable interiors. They came in fractional and masthead
rig versions. There was a masthead version that did quite well on the Bay.
Jeff