Originally Posted by SuperCriollo
Best bet it to try out some guns, and gear before spending money.
If this is an option for you, do it. Otherwise, go with VFC. They are quite good in stock form and as far as AR's go you can do practically anything to them and they generally will retain their re-sale value due to their higher quality.
To one of your other points, Ontario generally has a shit-ton of Milsim events going on with various levels of intensity. I suggest you go to a shorter Milsim like an eight or twelve hour one to get your feet wet before diving into a 18-24hr. Milsim's are all about endurance, you have to make it until the end!
However, since we are now heading towards winter, the season is going die down for these games.