Hi everyone, im new here in Canada, so sorry if my english is not very correct

I do off road for more than 8 years, i used to have a samurai and a Daihatsu Feroza. quad and mx bikes just lost count of it. So im looking to find a 4x4, the Wranglers had always been a 4x4 i wanted to buy one day, so why not now? i dont need a car to ride every day, so gas is no problem. i've been looking at some wranglers and cherokees sport, can you guys tell me what are the most important things i should notice about? i always drived manual gear box, so is it auto a good choice? is it legal to have big tyres? like 33/35 and so on? and finally is there a track or a place near toronto where people gather around for a little off road?
sorry for the big statement.