Reddit reviews The Best Used Boat Notebook: From the Pages of Sailing Mazine, a New Collection of Detailed Reviews of 40 Used Boats plus a Look at 10 Great Used Boats to Sail Around the World

The book below makes specific suggestions on bluewater capable used boats. The list is far from comprehensive but it does give as good overview of pricing and history of the boats. With a few exceptions, the boats are affordable (I know that's a relative term when it comes to sailboats). Here's the book (clean link)

https://www.amazon.com/dp/1574092340/

Your budget will limit your choices, but there are "crazy" deals made every day in the sailboat market. I too am looking at sailing away in the next 12-18 months. I met a guy recently with a beautiful Hans Christian 38. He bought it, put a ton of money into it, but turns out his wife doesn't like overnight sailing, never mind bluewater sailing. So he'll be selling. This scenario plays out every day. Get the word out that you're looking as you get down to 18-24 months from leaving. Be prepared to move quickly and have the cash lined up.

The list in the book was compiled by John Kretschmer who is one of the most experienced bluewater sailors out there. His book "Sailing a Serious Ocean" is a good read as well.

Good luck on your journey!

I hear you. If I were going to start looking for a passage making boat today, I'd start with this and this.

Then I'd look here and see what others are doing. If you're going to go small, I personally like S/V Prism and their Hans Christian 33. On the opposite side, S/V Delos is a gigantic Amel Super Maramu. But La Vagabonde crossed the Atlantic in a Beneteau, so you have a lot of options (not even counting catamarans). In your case, resale value is probably more important, so an older boat might be better.