I can't talk about the Catalina that you are looking at, but I can talk about the process. I am closing on my first sailboat tomorrow afternoon. It a process I started in January. I am buying a 1977 Endeavour 32. This is after looking at a lot of boats in the size and price range I was hoping for. The first thing I did was determine what I wanted for a boat. I also spent a lot of time reading everything I could find about boat inspections. I knew that didn't want to spend $600 on a inspection unless I knew for sure that it was the boat for me and that there wasn't going to be any big surprises with the inspections. I started with a book called Your First Sailboat. It has a lot on information about what to look for. It also has a section called the 30 minute inspection. It tells you how to inspect a boat and what to look for. There are also a lot of inspection tips in the forums. The bottom line was, when I stepped on this boat, the first time, I just knew it was the boat for me. It just felt right. I then read everything I could on Endeavour 32. I got a review from Practical Sailor. So I knew what owners and reviewer were saying about the pros and cons and how it would sail. I also went over every inch of the boat, doing my own hammer test, checking every compoinit, looking for water intrusion. Once I was satified, I made the offer. The first offer fell flat. I knew the boat was already priced low, but just needed to get that better deal. I went back with a new offer, this time meeting the sellers price, but asking the amout to escrowed, in the event that issues came out of the survey or shakedown cruise. The seller went for that. I ordered the survey and it came back with only minor suggestions. Stuff like hose clamps needing replacing. That's my story. If you want more information feel free to ask.