There’s a book called “The Contrary Farmer” by Gene Logsdon, which is a pretty good resource if you’re interested in small scale farming anyway … but from memory there’s a chapter in there on tractors.
As I recall, the best advice was somewhere along the lines of, “find a local who knows about tractors and ask them”, but there’s a bit more than that.
My copy is pretty old, so you might need to look for it second hand … or maybe not … here’s the book, and chapter 9 is on cottage mechanics.
There is also a section on farming with horses if you’d like to give it a go … apparently horse-power is making a comeback. I know of one commercial potato farm in Victoria (Australia, not Canada) which uses horses.
And in the US as well it seems:
And here’s the small tractor FAQ:
A bit of Googling reveals: “your first tractor”:
http://www.newfarm.org/columns/gd_tractor/2005/0421/index.shtml and part two
And there was a Usenet board out there somewhere called something like rec.rural or alt.rural, which is probably now on Google groups, which which would an excellent resource, if a little touchy.
I had a quick look, it’s misc.rural and this is the search for tractor:
There’s a lot of tractors there.
I think if you use Google to good effect with terms like “small farm”, farmlet, “small acreage”, you’ll find a lot of advice.
Good luck … I moved onto twenty acres in a small rural town, from the big city three years ago, and I still think it’s the best decision I ever made.