My suggestion is to go for Canada. Vancouver is very nice (mildest weather) and there's this great website -
Vancouver lofts for sale and rent - LoftsVancouver.com - that is just THE BEST if you're interested in buying or renting a loft. Gastown is a nice area full of restaurants, bars, and shops - great walking/strolling area. For nice beaches you can pop down to Mexico - Cabo is great, less than a 3 hour flight. Good Luck, Zoom