OH, this is fun....I wanna play....
A couple of years ago I was looking to get a daily driver so the VX could become the garage queen that I always wanted her to be. I too was looking at one of these

because it's basically a VX with a different skin. I figured that I would still be able to hang out with The Fam, but I would have to be at the back of the line while wheelin'. Instead of buying an Amigo I ended up having this

built and I haven't regreted it for a second.
If you do end up selling this

to get this

just realize that there are some other things that you will need to invest in such as this

this

this

this

and this

I know Gill rides so you may already have some of the afore mentioned items, but eventually you will need to get one of these

and last but not least you will DEFINITELY need to get one of these

On a sort of serious note; you may want to try and find an Amigo/ Rodeo Sport with a removable hard top as the soft top may be cold, and may get chewed up, in those Chicago winters. The Harley would definitely be fun, and you, Gill and I would need to find time to ride together. If you could swing it having the VX AND the Harley would be the way to go (for me), but either way I'm sure you'll have a great time.
"The major difference between a thing that might go wrong and a thing that cannot possibly go wrong is that when a thing that cannot possibly go wrong goes wrong, it usually turns out to be impossible to get at or repair."
-Douglas Adams, Mostly Harmless