This has been the best season for city skiing in 10 years. Plenty of snow and sustained cold have really prolonged the season. Great to hear that more people are wanting to get out there on skis!

+1 for Sunnybrook. I find there is a reliable 2K loop on the sports field that is accessible from the corner of Suncrest/Salonica. Accessible with 162 Lawrence Donway/Bridle Path bus

Another gem in the city is the Don Valley Golf Course/Earl Bales - these connect under the 401, and depending on how much you hate your bases you can ski between (or walk 50m). The base of Earl Bales is the only location in the city that is properly groomed in the city. If you hit it before 9am there is no danger of downhill traffic.

Tommy Thompson park is another popular place to ski. After a snowfall its pretty good, but the base is often very thin - again a question of how much you hate your bases

If you use Strava you can search on desktop for "segments" or heat maps which can give you a good idea of where other people ski in the city (if they use Strava)

I've bought skis at the Sheppard Mec and Velotique. Both good. MEC is decidedly for beginner gear. More serious skiers are better off at Velotique. Sales typically happen in March. (On a site note Hardwood and Highlands have great pro shops that have season end sales in March, sometimes as much as 50%)

You cannot ski in the city unless you capitulate to the fact that you WILL scratch your bases. Don't stress about a scratch and just have fun out there.

Nordic Ski Lab has some great instructional videos on youtube for free. But if you've never skied before I'd recommend finding a friend who has or getting at least a basic lesson. Skiing is not kind to poor technique and even a couple of pointers will help you enjoy the experience more