Why did I decide to start telemark skiing?
My quick answer:
-new challenge and good workout
-snowboarding icy groomers really isn't much fun
-split-boards are too expensive, and I wanted to earn some turns climbing uphill and getting fresh pow runs.
First off, I love snowboarding. On a really snowy day, it will be tough for me to turn in my board for my ski's. If you are thinking about (seriously) learing tele or learning to snowboard, snowboard. If you just want to do it for one day, tele may be less painful.
I love a new challenge, and being on that learning curve. The prospect of starting over at the beginning is humbling, but it makes you stronger. Tele skiing is a great workout for my quads, it makes me a stronger snowboarder, it works my quads so when those powder days come, I'm ready to rock. On a mountain that is relatively flat or boring, or when I'm spending time with friends that go skiing about once a year, tele skiing is much more fun than waiting for them mid-run or at the bottom.
A typical new england day, isn't always a powder or packed powder day... The less powder and snow on the mountain, the more I'd rather ski... Two edges has advantages when there isn't much to grip.
After some point in your skiing career, you get spoiled. You start to have 'powder-greed', this greed drives you try to time your days on the mountain with big snowstorms. While fresh powder on resorts is typically gone within hours, the snow is still out there sometimes several days after the storm on less-traveled and mountains without lifts. This brings me to uphill/downhill, I'd hike a mountain and snowboard down it. Snowshoeing up isn't a bad way to go -- although the best way up, is to get a splitboard with skins. This setup can be expensive though. I found a used telemark setup was a bit cheaper for entry-level.
There is a rhythym to the tele turn that is invigorating, linking a few turns, feeling good, can be a great experience. I sometimes find myself walking down city streets, with each footstep bringing back a memory of some great tele turns.
Oh, and since you may not be on the mountain with too many others, bring a friend and some spare parts...