I am a recent (December) and unemployed college graduate, and after spending 22 years of my life working my *#$ off for a career in finance, only to watch it all evaporate before my eyes, I've had enough with land life and want to sail around for a few years and "weather out the storm." I have 20,000 at my disposal, so 14-16 for the boat and the rest to make the necessary improvements. My plan is to sail the great lakes/intercostal while I cut my teeth, then maybe onto more ambitious endeavors. I have crewed/sailed J24s since I was a kid, but have never done any bluewater.
Since I will be singlehanding and have a somewhat limited budget, I was thinking in the 24-28 foot range, I know Cal 27, Cape Dory 28, Saber 28, etc. are great boats, but may be hard to come by in my price range and should look for something smaller?