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I'm going to throw something out here you haven't considered yet. (and I think you have done your homework pretty well)
What about a Maxi Scooter? Something like a used Suzuki Burgman. They have a huge storage compartment built in that will hold 2 full face helmets. With a 650 cc engine they will haul two people on the highway. You might even get your wife to ride it by her self since they have an automatic transmission. That would allow you to get another bike for yourself. Use the scooter for commuting and a sport bike for weekend runabout.
A search of Cycletrader shows a bunch of ~10 year old Burgman 400's with fairly low mileage for less than $3,000 asking price.
Also want to add, I have a 1997 883 Harley Sportster with the mid mount controls, it is not the feet forward position of most cruisers. Easy to find them in the $2,500 range. However if they have any storage on them it is usually just leather soft bags which are not lockable. Hard bags are an option, but not cheap. I commute on my almost daily in the summer, but I use a backpack and bring everything into the office.
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