I've just moved aboard myself and found myself going over and over different boats that I could get into around the same range. My plan was to find something, fix it up while using it and then when I'm finished with school sail off into the sunset.
In the end I changed my mindset a little. I stopped thinking that the boat I was buying was going to be my boat for the next 5-10 years.
What I decided on was a boat that's considered a good coastal cruiser and has lots of room for 30 feet. In the end it narrowed down to a Catalina 30 or Newport 30 II. They are very similar in width, sail area and all other numbers.
Finally bought the Newport 30 because I've known the owner for a long time and knew he had always taken good care of the boat.
Point is...I love the boat, it'll give me a lot more experience in sailing (had a Catalina 22 before) and then in another 3-5 years after I've got some experience coastal cruising I'll look for another boat, something more geared towards bluewater cruising.
Don't get stuck in the mind set that the boat you buy is the last boat you'll own.