I am going to resurrect this thread like Dr. Frankenstein for a 500-mile report, as I have now been on the Shetland for 5 weeks, everything from commuting to whipping down the expressway to farting around town to trailer towing with the family.
Longest ride so far: 24km. Longest day on the bike so far: 41km. I haven't had the time to break that yet.
As shipped, the only weak point for the Windsor Shetland is the tires. These Kenda Kriteriums are pretty inferior. I have averaged one flat a week (not counting a couple from user error). I threw some Slime tire liners in yesterday to see if that helps, but after that, it's straight to some Primo Comet kevlar belted 451x28s. If the production bikes still have 451s, maybe Kenda Kwests or Primo Comets would be a better way to go. I'm not so sure about the BB (which, by the way, takes a 14mm socket to remove the cranks)... I might replace it with an SRAM unit I have laying around.
Everything else is excellent, though.
- I have no heel strike on the panniers unless I am wearing my slightly-too-large cycling sandals AND the panniers are full.
- The shifters are in a great spot, in spite of how they look to the uninitiated.
- The original seat is pretty good. I think I'll keep it.
- It fits on our Thule Hitching Post, but it makes the Honda Fit look huge.

Haven't tried it in the back, though.
- It almost doesn't fit on the vertical hanging racks on light rail, it's so short.
- towing the trailer was a piece of cake... and I could do u-turns on the MUP with room to spare
Overall a very fun ride.