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I'd definitely use the shotgun more. I enjoy hunting and skeet shooting, but my only shotgun crapped out a few years ago so I've been doing without. I like my 40 a lot; I just don't use it. I don't get to the range much and fortunately I don't have a home invasion problem I have to handle regularly. I think I just might go for it.

I've been told size doesn't matter. Sometimes, I wonder if my wife just says that to make me feel good though...

I'm by no means a scooter expert.  In fact, this is my first one.  I can tell you anything you'd like to know about my specific experience buying my Evo.  I've put up a thread or two about it.  In a nutshell, I've been 100% thrilled.  Like Matt said though, if you have any specific questions I'm happy to help however I can.

Rich, you got me thinking about your remote admin conundrum. What if you stripped his software down to bare bones, then had him remote in to a computer that physically is in your possession? That way, you've turned the tables. It sounds like he needs restricted access and you need full, even hands-on, access. You send him a refurb $100 machine from TigerDirect and have him send you the one you built. Take every single application off his physical machine and leave him only with a Remote Desktop icon. If you wanted to get super crazy with it, you could only allow him to remote into a virtual machine, which you could just fry whenever he loads it up with malware. 

My kids are still a little too young to have unsupervised computer time, but a buddy of mine does something similar with his kids. He has a virtual XP machine that is the only means of connecting to the internet. He doesn't even run anti-virus on it. He keeps a ghosted image of the machine and "flashes" it with the ghosted image every couple weeks...good as new again.

 If you turn down their "freebies", which I think is a helmet and gloves, you get a discount.  Also, if you pay cash/check/money order...basically anything but plastic, you get a 3% discount.  They also offer a military/police discount.  I was able to take advantage of all three.  That brought their TaoTao 150cc "Cruiser" which is actually a TaoTao ATM-150A EVO, down in price from the listed $929 to $843.  

As far as having a Dash equivalent, KMS has the same scooters every other Chinese re-seller does so I'm sure you can find it there.  

Personally, I wouldn't want to go smaller than a 150.  My 150 is pretty nimble up until about 45 or so, then it will slowly creep up to max speed from there.  It's perfect for around town.  I can easily pull away from traffic on a green light so I'm out in front of everyone.  That certainly makes me feel safer than when I'm having to monitor all the vehicles around me for careless lane changes.  I don't think the same would be true for a 50cc.  Sure, the top speed is listed at 35 or something, but if the 50cc performs similarly to my 150, that wouldn't be fun in traffic.  Maybe it'll do great up until 20mph and then struggle the rest of the way to top speed.  I don't know.  I don't own one.  

Insurance on my scoot is $10/month.  Here in IL, it cost like $100 or something to get it titled and registered.  I didn't think that was bad.

Good luck!