Maxum pretty much nailed it for you. The only thing I will add is on the trailer definitely an enclosed one and I would go with the hybrid style with a ramp. I have a clamshell and find them a bit frustrating. The two up is a long sled so you will be looking at a 12ft clam. Even with just a couple inches of powder on the clamshell that adds a lot of weight and you have to clear it off to raise the shell. You also have no head room in trailer to work on the sled and even with the clam up I can't fully raise my hood in the trailer. The weight of 12ft clam is tough on the assist shocks that aid in lifting it up so the shocks don't seem to last long.
If cash is no worry consider buying two singles vs a two up. You can always sell one if your wife doesn't like it. I have a two up and my wife didn't really take to it and I wish I now had a single. Like maxum said the 4stroke 2up is a big heavy machine that loves the big wide flat groomed trails in pittsburg but not as much fun on the narrow twisties around the lake. The only other comment on a 4stroke is the oil changes can be a project. You may want to have a 6 pack on hand for that!
Also clothing - you get what you pay for and it is expensive. Make sure the wife is warm and dry or you won't be riding long. I saved a lot of money by buying everything at the grass drags in October. The vendors have good prices and left overs.
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