In reply to first post, big question, I can say go cruising as soon as you can. We're not getting any younger! So, I would suggest to stay away from a lightly built cruising boat such as a Hunter or Catalina. Think about an older cruising boat, better built such as an Endeavour 32, Pearson 32, Dufour 31 or an Oday 31. As long as they have been constantly maintained and upgraded, these boats offer alot for a little money. There are plenty of other production boats that would fit the bill as well. ALSO make sure you get a good survey from a surveyor that specializes in sailboats.
Keep the dream alive and good luck.