I was in a similar position back in 2004. I bought my first boat (1981 Catalina 22) in 2003, sailed for the rest of the season (Long Island Sound), half of 2004, then decided I wanted a bigger boat.
I wanted a boat with inboard diesel engine, wheel steering, marine head, hot+cold pressure water, self tailing winches, roller furling headsail, shower, and beds for 5 (me, my wife, and our 3 kids, who are young). My research showed that I needed a boat around 30', so I looked at boats in the 28 - 32' range. I am not interested in racing, but I do value performance. My budget was around 20K. I looked at a lot of boats, including Catalina 30, Islander 30, S2 9.2A, Irwin 30 and 32, Newport 28, Ericcson 28, Hunter 31, Oday 31, and a few others.
I'm not an expert, but to me, the boats were all basically the same.
All the boats I looked at were from the early to mid 80's.
Here are some of my opinions:
-The Irwins were lightly made and poor quality. I have no desire to cross oceans, but the Long Island Sound in the spring and fall has 20 kt winds and 4' seas. I didn't feel like the Irwin would do well in those conditions
-The Hunters from the early 80's were not made well. The boats I looked at were unattractive (personal opinion) and did not hold up well.
-Catalina 30 - great boat and my #1 choice. Well made, simple, lots to choose from.
-Islander 30 - nice boat, similar to the Catalina, but more difficult to find.
-S2 9.2A - I really expected to love this boat. Practical Sailor rated it very high. I looked at 5 of them. All had bad leaks around the chain plates. The boats I looked at (at the lower end of the price range) had moldy interiors, and were 'stripped' of things like hot water heaters.
-O'day - nice boat, but definitely built on the cheap side. Few had traverlers that could be adjusted under sail, most had pins that require you to move the pin, then tack to most the traveler. I also don't like the teak toerail - too much maintenance.
Ericcson - nice boat but the one I looked at had a tiller.
Newport 28 - I originally discounted the Newport since I looked at a bunch of 27' boats (like Catalina 27) and ruled them out as too small. I was in a yard to see an S2 (which was junk) when the broaker pointed out the Newport to me. I liked it. It met all my requirements. It has some nice features that the Catalina didn't have, like teak and holly sole, teak interior, cabin liner, self tailing winches, etc. Compared to the other boats I looked at, the newport was cheaper and in better condition.
So I bought it and sailed it home.
I'm very happy with the Newport, and you should consider them. The 30' is basically the same boat, just a little bigger. Nicer inside than a Catalina 30 and cheaper too.
If you can spend 30K you should be able to find a boat in good condition with good sails, good electronics, nice interior, etc. For that money, you may be able to get a boat with a swim platform / boarding platform. That would be nice to have.
One last thing, my 1986 Newport is for sale ($16,500). I'm moving up to a 33-36' boat. Let me know if you would like more information.
1986 Newport 28
Mt. Sinai, NY