Re: Boat recommendations for a Newbe
I think it's helpful to get a few specific recommendations. As you research and shop around for those specific boats, you'll become familiar with their features and may start to spot others that would provide the same benefits. You'll start to develop a feel for what you want to pay for and what you don't care about.
The big piece of missing information is how much you want to spend.
Last year I started shopping for my first boat, and I was initially focused on the Bristol 27 and the Alberg 30. These are similar boats, designed by Carl Alberg. The Pearson Triton is also similar, and also designed by Carl Alberg. These boats are probably a little more difficult to find than others, but they have a good reputation and, because of that, they tend to sell for a bit more (rough guess, $8-$15k for the Bristol and $15-30k for the other two.)
While zeroed in on the Albergs, I happened across a Craigslist ad for a Cal 2-27. It was about half what I would have paid for a low-end Bristol 27. I looked at it that afternoon and bought it the next morning. It's been the perfect boat for me, my family, and my budget. It is very different than those other boats and doesn't have the same classic looks, but it does have a reputation for being bullet proof and it's a pretty nice family weekender. You ought to be able to find nice examples of this boat for less than $8k.
So, bottom line: collect some ideas, shop around, walk around every boat yard and marina you see, and be ready to strike when the right boat comes along.
Oh, and good luck lasting 7 years without an upgrade!