(This is response that I wrote for a different venue. If you actually have more experience than most people looking for a first boat today, I would sugget that you look at the higher performance designs below (noted with an *))
There is no more controversial a question than what is a perfect first boat. To begin with all boats are compromises. They are compromises between optimum sailing ability and the need for accommodations or shoal draft. If a boat gets wider it gets more stable up to a point but then it has less reserve stability to right itself if it goes over. If a boat is too wide and blunt, it has a lot of drag but lots of room down below. If a boat is too narrow it has less drag but if too narrow won't have much stability or room down below. Too much weight and the boat is slow and hard to handle, too little weight the boat is fast, fun, and easy to handle up to a point but at some point takes greater skills and athletic ability.
If you ask a bunch of sailors about the ideal first boat, some will suggest a small daysailor or dinghy. If you are in good physical shape, don’t mind being wet, live in an area where it is easy to launch and sail a dinghy, it provides a great platform, if not the best platform, to learn the basics quickly.
Other sailors will recommend a traditional design because they are a bit harder to get into trouble with. Here I strongly disagree. I really think that the ideal beginner boat should be responsive enough that the neophyte can learn proper sail trim and boat handling.
Over the years, I have taught a lot of people to sail and I firmly believe that to really learn to sail the boat should be light and responsive enough that you can experiment with sail trim and sailing angles and be able to see and feel the results. I find that for most adults the best beginner boat is a boat with a reasonably easily driven hull and a reasonably modern sloop rig and fin keel-spade underbody. I find that fractional rigged sloops are really the easiest to teach proper sail trim on.
I think that late 1970’s era, obsolete MORC racers make great teaching platforms. They had robust and easily maintainable rigs and hulls, they generally had better deck hardware than more modern designs or than cruising designs of that era. Race boats are generally better maintained and come with better sails than cruisers. The myth of the rode hard and put away wet is generally based on grand prix level boats that have little value once obsolete rather than the more common production racers. I do not recommend buying one in fully optimized race condition as that generally implies specialized maintenance and a higher purchase price.
Of course, the right choice clearly depends on the neophyte’s own priorities. There are a lot people out on the water who really only understand the rudimentary aspects of sail trim and boat handling. They may only care to know enough to safely get out of a slip, sail about and get back home. Over time they may develop survival skills cruising skills and in my life I have met many a distance cruiser who really understands little beyond the basics of sail trim. If that level of skill works for them, then frankly who are any of us to judge them. We all come to sailing with our own goals and priorities and there is no one universally right amount of sailing knowledge required.
But if the beginner really wants to learn the fine points of sailing then I would suggest sticking to a sloop, 30 feet or less in length, of light to moderate displacement and with a fin keel and spade rudder. Beginners sometimes think they prefer wheel steering, but on this size boats a tiller is far and away better both to learn on and to sail with. I generally recommend against centerboard trailer-sailors because (with few notable exceptions) the sailing ability of these boats really is not ideal for a good learning experience.
This first boat should be viewed as a learning tool to develop not just sailing skills but the skills necessary to own a larger more complex boat. This first boat will also help you develop a sense of what traits you want in your next boat. People tend to hold onto first boats for comparatively short periods of time. I therefore suggest focusing on older used production boats, as these can more readily be bought and sold with minimal cost or fuss.
Of course it is also important to figure out where you are going to sail, since different sailing venues favor different types of boats.
Here is a list of some good basic boats that depending on the individual should make good first boats : (These should all be available for less than 25K, most have inboards which I think is preferable for cruising.)
-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 an ideal first boat. They are reasonably fast (although 60 sec's a mile slower than my Laser 28) and easy to handle. They are nicely finished and typically have diesels. The interiors on these boats are not exactly plush but are reasonable for the kind of stuff we do here on the Chesapeake and on much of the Atlantic Coast.
Beneteau First 30 or 30E (30 feet (early 1980's) $18-22K)
These are a fairly modern design that should sail reasonably well. Not the most solid boats but fine for most venues. 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/space rudder boats. They are really not competitive racers any longer.
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.
Catalina 27's: Venerable, common and cheap to buy. I have been sailing on these boats for quite a few years now. They are not especially well built and tend to blow up hardware but then again the Cat 27 that I sailed most on was a 15 year old boat that had been raced hard for much of its life.
Dehler 31 (31 feet (Mid to late 1980's) under $20K to mid-20K range)*
These are really neat little boats. They are not as fast as my Laser for example but are quite 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 for a first boat that can be both cruised and raced.
Dufour 2800 (28 feet (mid 1980's) mid $20K)
These are OK boats with a reasonably solid following. They are not my favorite but they would not be a bad boat if the price were right.
Farr 1020's (34 feet (Late 1980's)
These are really nice 34 footers that have a reasonably complete interior for more extended cruising and are quite fast and should be easy to handle. They are a little big to be ideal for most beginners.
Late 70's/ early 80's Hunter 30's, (30feet (15-20K)
These are 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 successfully in PHRF. They are roomy and surprisingly fast.
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 like the Hunter 30, you are looking for a well maintained example in reasonably good shape.
These were part of J-boats 'cruising series' along with the J-34c, J-35c, J-37, and J-40. These are nice little boats and would be a good choice in a windier cruising ground. They have a nice layout and seemed to be nicely finished.
J-30's (30 feet (Late 1970's on) $20-35K)*
These were originally built as 'hot' race boats and in their day they were really quite fast. Today they are seen as heavy and under canvassed. There are a number of model changes over the years and some resulted in a pretty nice cruising layout. These are good sailing boats but somewhat brutish to sail compared to some later high performance boats. Ergonomically they are far from my favorite boats, BUT they have a strong following. Their perennial one design status has held their value up quite nicely. They have diesel auxiliaries and are pretty easy to find. Be careful of problems with their coring as the Balsa cored and some of these boats have had a very tough life.
Kirby 30: (30 feet (Late 1970's-early 1980's) $12 to $25K)*
These were really intended as race boats but they do have an interior that can be cruised for limited periods of time. They are one of my favorite boats from that era. (I owned a Kirby 25 which was a smaller version of the 30).
Laser 28's (28 feet (Early to mid 1980's) $16to24K)*
What can I say, I love these boats. I have owned mine for 13 years and she has been great as a racer, daysailor, weekender and cruiser for periods up to 11 or so days. They were boats that were a decade ahead of their time. Many are Kevlar/Vinylester construction which is a really tough act to beat in terms of durability and light weight. They had a clever interior with a nice galley and head. Many have pressure water and a shower and a few have hot water heaters even. They have a nice little Buhk diesel. After 13 years I had no doubt that this was the right boat for me.
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 Laser 28. They have a diesel aux. They have tiny tanks that will need to get upgraded.
Oday 28 & 30 (28 feet and 30 feet (late 1970's and early 1980's) $12-20K)
These were not the best built boats or the fastest boats in their day but are common and sail reasonably well.
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.
Tartan 26's: Quite rare little boats. They are nice to sail and have reasonably comfortable interiors.
(Other Tartans to look for are the Tartan Piper and Tartan 31 but these are more expensive boats)
These are simple, readily available keel boats. They offer reasonable build quality, decent sailing ability and a cheap price.
70's vintage Pearson 30's (Not Flyers)*
These are very venerable racer/cruisers on the Chesapeake. They have an active one-design class and are also good boats for cruising the Bay. 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 Flyers: (30(late 1970's early 1980's) $12-20K)*
These were intended as competition to the J-30. They were reasonably good boats pretty much on a par with the J-30 in many ways. They have not done as well in racing since they do not have a one design class to help perfect the Breed.
Ranger 29 (29 (early 1970's) 10-18K)
These are good sailing and nice cruising little boats. They should be adequate for club racing and are certainly good 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.
Sabre 28 (28 feet (1971 to 1986) $12-30K)
They have a reasonably high quality build, and are still supported by factory, with over 500 made The S-28 is one of the few boats which meets the ORC capsize screen under 30 feet. Nice teak interior and somewhat classic lines.
Shockwave (also called Schockwave 30, or Wavelength 30 )*
Pretty stripped out racers but really neat boats. They are quite fast and should be a lot of fun to own. They did have a sort of high tech interior that lacked elegance but worked reasonably well.
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. There was a one design version called a Hawkfarm. They never caught on the Chesapeake but are still raced in S.F. Bay.
If you want some thing more traditional
C&C Redwings and Corvettes
Pearson Coasters, and Wanderer's
You will find that these traditional boats have less room and will have older equipment but they should be less money and may be better sailing boats than some of the newer boats on the market today.