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If you ride 2-up frequently on longer trips you'll be better off with a touring model, even if it's a few years older. No cruiser is going to be comfortable for a pillion for hundreds of miles a day, they just aren't big enough.
Take a look at the cost of replacing the shaft drive unit on those Yamahas. Not saying they fail often, but it does happen, and it's not a rebuild-able part. About $1500 just for the part, if I recall, and the engine has to be torn down to replace it. I wouldn't let it keep me from buying one, just something to consider.
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