Triples are very nice for around here. It's not so much a matter of fitness and experience, it's a matter of HILLS! (one of my bikes is a compact double and one is a triple. I'd definitely take the triple on ALC or STP or RSVP or ...)
I went for a good long ride today in the rain, but I was on my triple with full fenders and buddy flaps. Wheeeee! Considering our weather, you might want to be sure you can get fenders to fit the Ruby. And buy those fenders the day you buy that Ruby so you don't have to wait even one second to go for a ride!
When you do your test ride, be sure to go for a long ride. My LBS lets me wander off for 10-15 mile test rides, which I love cuz otherwise I just can't get a really good feel for a bike. Take it zooming on some flats, slow-poking in a parking lot, uphill, downhill. Shift through all the gears and see how the shifters feel for your hands. Assume you will replace the saddle the bike comes with, don't let the saddle bias you.
Have fun! And ride a few other bikes just for the experience! (how about a Surly Long Haul Trucker? It sizes down to a 42.)
"If Americans want to live the American Dream, they should go to Denmark." - Richard Wilkinson