Sounds like a blast!! Been getting the bike itch myself.....any recommendations for a beginner bike (preferably Harley or similar type cruiser...not a fan of crotch rockets) and i do mean beginner...like never ridden one! (do mopeds count?)
The smallest of the Harleys I would recommend is the Dyna Glide Series. The Dynas are the smallest (same engine size) of the HOGs and great looking Bikes (I'm partial to the new DYna Wide Glide). They are NOT the greatest Bikes for long distance touring but not bad. You and your wife can ride locally pretty comfortably on one of these unless you are a huge guy. The Dynas are also on the bottom end of the HOGs cost wise.
I personally have a Road King and love it for a lot of reasons. The wife loves it and other than her butt getting sore, we can travel long distances comfortably on it.
As for learning to ride..... try to find a smaller dirt bike or street bike to learn on.... say a 125 or 250.
PM me with any questions you might have!