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Back in 2004 I was in a similar position. I had 3 kids, girls 10 and 7, and a 3 year old son. I had a Catalina 22 which was great for day sails but I wanted to go somewhere for a weekend and the C22 was too small.

My requirements:
Decent sailing ability (I didn't even know what that meant at the time)
wheel steering
self tailing winches
roller furling headsail
Standing headroom
Inboard diesel
marine head in enclosed space
hot and cold pressure water
small galley
bunks for 5

I looked at Catalina 27 and found it too small. I looked at Catalina 30 and it was perfect. I was not able to find one in my price range. I looked a bunch of 30 footers: Tartan, Pearson, O'day, S2, Lancer, and a bunch of other odd ball boats.

I went to one broker to see an S2 9.2A. It was junk but the broker suggested a Newport 28 he had. It was JUST big enough and had everything I needed. I bought it and it was great for a few years. Great for day sails. Good for a weekend. The problem that that with three kids, once you were in 'night mode' it was just about impossible to walk from the back of the boat to the front of the boat.

Anyway I would suggest you look at a Catalina 27. Some come w inboard diesel. If that's big enough then you're set. It not, look at some 28' boats like O'day, Newport, etc. I would strongly suggest an inboard diesel over an OB, especially if you plan on making long(er) trips. A Pearson 30 might work for you. Sweet sailing, Small for a 30' most have tiller,

Good luck,
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