Another happy customer and friend of Peter Ricks here! We started out as a business acquaintance, and we now count him and his wife as friends.
Since you are handy, consider this boat, advertised in the classified section:
https://www.trawlerforum.com/forums/s9/albin-40-trawler-70365.html
Check some, but not all of your blocks. Great starter boat, can't beat the price, and it'll do Loop or Bahama's no sweat. It IS a single though, and you said your looking for a dual engine.
On Flybridge, if you are NOT planning on doing the Bahamas, I wouldn't get too wrapped up over not having a flying bridge. But that's just me. Best of luck!
One last item. If the boat you buy is some distance from what your home base will be, consider hiring a "delivery/trainer" captain for part or all of the trip. You will a lot more value out of an actual trip IMHO, than in a few, couple of hour trips out of the marina.