The iTrips work very well for an FM transmitter. As long as there is an available frequency in your area, you shouldn't have any trouble. Apparently some larger cities aren't so good for them, but Winterpeg should be fine.
My only problem with the iTrip are all of the small files it needs to load onto the iPod to set the frequency. If you use the Party Shuffle in iTunes, or shuffle all of the songs on your iPod, these will be played too. I know you can set up a smart playlist with everything except these, but it is still annoying.
goates