If I were to till with the loader and bucket on and end up at 2700-2800lbs is that enough weight to keep the tiller from kicking as long as I'm going the appropriate speed for how hard/tough it is?
That depends on how heavy a tiller you buy, how quickly you want to till your soil and how moist the soil is when you till. Much of this is Newton's Law about equal and opposite reactions. Heavy equipment dampens shock.
I recommend at <26 horsepower tractor to avoid the expense and complexity of Tier IV emission controls.
If you need a front PTO and MMM the Kubota LX 2610 would fill the bill, though it is a little light at 2,000 pounds bare tractor weight. Even with filled rear tires the tractor will bounce around operating a PTO-powered, forward rotating roto-tiller
in hard ground. You will need to roto-till in fairly small increments, several times.
Land is fairly flat, any hills are subtle.
If you have ample time, a 2,000 pound bare weight tractor will serve you well on five acres.
If you forego the front PTO the Kubota
L2501 is wider and heavier at 2,700 pounds, therefore a more stable machine. A 2,700 pound tractor will operate a roto-tiller 12" wider than a less stable 2,000 pound tractor with the same horsepower.
In any tractor line, 2,700 pounds bare weight is when a $400 FEL Bucket Spade becomes an effective tool. Really good for planting trees.
If your budget permits and you have enough storage space nothing wrong with a heavier tractor and more horsepower. I know not your altitude in Saskatoon but if over 4,000' calculate altitude power loss when determining gross tractor horsepower required. The well-informed opt for a tractor engine turbocharger at 5,000' or higher.
For planting trees i recommend renting a skid steer with an auger for a day or two at a time. You could auger in a lot of holes in a day then plant your trees and backfill with any small tractor.
== YES ==