Did you mention what your other bikes were? At least one MTB... others? How many road bikes?
How is security for your commute? Much less traumatic to loose a $50 bike than a $1000 bike.
I think I'd either buy the Kestrel, or hunt for a good used Titanium or CF road bike. Then upgrade the Panasonic if you choose. Oh, do you need a rack on your commuter?
Some things like Jockey Wheels are consumables, and need to be replaced when they wear out. I'm not sure about your dropping the chain. If no obvious issue, it could be adjustment, or even simply a derailleur that has rotated on the mount.
There are "chain catchers", or perhaps it would give you enough of an idea to make one.
Do you have a local bike co-op or bike recycler? Some of the parts you need may be available there for less than new prices... sometimes even scavenging parts from busted derailleurs.