When the Ural was introduced into the USA in the late 70s or early 80s (can't remember), one of the big motorcycle magazines did a long distance test on one. Their intent was to run it 5,000 miles while evaluating. Their final report: "We give up, at 622 miles. They couldn't keep it running, parts kept breaking." OK, I was curious back then. But I wouldn't have bought some pinko commie fag bike. Another nightmare of a bike with a side car would be a Royal Enfield. Since you are a good wrencher, you could help her with her maintenance. Also, the Enfield has a solid drive axle which also drives the sidecar wheel. Sorta like an open SUV. I'd get the 500cc model. Remember Soren, these things have to be tinkered with.
Now, if she wants a real fun ride. The Honda 750 MotorTrike "Scooter" is the way to go. 7" Ford rear end with air suspension, bulletproof reliability, and the best looking trike on the road. Drawback: $15,000. This is what my wife wants, but I'm trying for a R-3 and give her the America with an Insta-Trike kit.