There is much in the way of good advice here. My Admiral and I just spent a year looking for a larger boat to extend our life on the water. Started with some misconceived ideas and learned a great deal on the way. If I may, here are some suggestions:
1) First, because of the market, at the price you are talking include all boats in your search up to $60K at least. This is still a buyers market and many sellers are willing to work with you.
2) Forget about manufacturers and models. Look at everything in the price range that you have set. Each and every time you look at a boat make a note of the things you like and the things you don't. More the things you don't. On these do not compromise. Yachtworld.com has already been mentioned. This is your number one best source for looking at boats and determining what you like and finding out what is for sale. Also, Craigslist, BoatShed and Boat Trader.
3) As this will be a project boat and a live a board, imagine living on board when you view these boats. Don't picture yourself BBQ'ing and relaxing on the hook in some beautiful cove. Imagine the problems. If there sufficient storage, where will you put your cloths. Do you wear dress work cloths then you need to hang them and iron. What about laundry. If you are going to cook, you need counter space. Too many boats are not designed for long term stays. Putting up with inconvienences for a weekend, week or even a month of cruising is one thing. Putting up with them for years is a very different thing.
4) As you live in the PNW there is little time without dampness or rain, You need to consider where you will store things outside and if you intend to use the space outdoors to extend your living space. If so, then you need an enclosure. If a trawler, can you access it without going outside or must you go into the elements to get there. That may be ok but you need to decide what you want.
When we were looking we had to consider we have a Golden Retriever. She can;t climb a ladder to get on a high deck boat such as some aft cabins. Climbing up a single step on the transom off of a narrow swim deck was not a feature the Admiral wanted. We looked at many boats, we went round and round over a year and a half.
This was our adventure. Every weekend traveling to look at another boat. We must have spent a fortune on gas, eating out and motel rooms. But in the end we feel it was well worth it. I hope that this helps. I don't mean to make this sound negative. But one of the hardest things some people have trouble doing is taking off the Rose colored glasses and seeing what daily life can be.
Good luck in your search. We loved looking at all those boats and more so finding the right one. Which by the way ended up not being the style we originally thought we would end up with.
