Re: Caliber 28 vs. Island Packet 27 vs. Com-Pac 27
I'm surprised you didn't get any responses. I'm no expert but the Com-Pac 27 has always stood out to me (based mostly on interent browsing) for it's all around practicality considering both price and size. If I wanted to move up in boat size without actually taking on much more expense I'd consider it. I like it's solid look and think the simple aft head layout is ideal for that size boat.
The island packet is also a Bob Johnson design but it's 1' wider and 1 ton heavier. I think the build quality of the island packet is probably going to be better but the Com-Pac is unique for a 27 footer because it actually survived through the 90's into today. So unlike most used 27 footers you can actually find newish used ones if you want. I think that speaks to what I said initially which is that it's a good all around value.
Note that Bob Johnson boats are known for their comparatively large cabin size but not their sailing ability. Neither of them are going to be particularly quick. I don't know much about the caliber.