Bluegill: One of the best resources for new shot shell reloaders(experienced ones, too), is the Lyman Shotshell Reloading Handbook. It contains a wealth of information that you will find very useful in getting started. Plus, will be a great reference as you gain more experience.
Another good resource, is the online: Hodgdon Reloading Data Center. Geared more toward reloading data, but still highly useful. Will be helpful once you have a good handle on the basics.
There are likely more sources I've missed. Others will likely offer that info. But for now, this basic stuff should get you going.
Can't offer any advice on loading TSS. Have yet to reload any hulls using this shot. Have taken my fair share of wild turkey, though. Ordinary hard lead shot drops them just as cleanly. Plus a whole lot cheaper. Since you're in southern Ontario, you can likely purchase 25 lb. bags of lead shot for reloading(as well as wads, primers, etc.) , from either Hummason, or Lawry's.
You can roll crimp your shells if you like. Not hard to do. But, may find the process a bit intimidating, as a newcomer. Far better to start with the more widely used, 6 or 8- fold "pie crimp". This is the most commonly used form of shot shell crimp these days. Most load data will reflect shells built around this method.
You can buy pre-primed hulls. But...it's far easier and cheaper to simply re-prime your once-fired hulls. Most reloading presses offer a priming station, for just this step. Simple and easy to do. This step, as well as all other steps involved in the loading process, can be found in the Lyman Handbook.
Ballistics Products loading information is highly informative, too. Though heavily geared toward their products. A useful resource, but not as comprehensive as the Lyman Handbook. This source will be more useful to you once you've gained some experience.
As far as equipment goes, at the heart of shotshell reloading is a good, reliable press. Since you're a newbie, I'd recommend sticking to a very basic setup, to start. Your budget will reflect your choice. But....you can't go wrong with a Lee Shotshell Reloader. An inexpensive, basic reloading press that is capable of turning out good shells. Great little press to learn the basics on. I've owned and used one for years. Worth considering.
But if your budget allows, I'd recommend a basic, single stage MEC press. MEC Junior, etc. A big step up from the Lee. Fully adjustable and capable of turning out shells as good as....or even better, in my opinion....than factory loads. Will last your lifetime and beyond. Definitely worth the investment.
Ultimately, your choice will depend on how serious you are in getting into shotshell reloading.
Hope some of this helps.
Al