A's and B's are meant for cultivating small fields. They'll do ok with a sickle mower, or for plowing snow in a driveway. They should be left to those tasks.
Pulling trucks out of mud - pulling a wagon with people on it - sure the a/b/c's CAN do that in the right conditions, but you'll almost certainly be left wanting more tractor. The problem is they just don't have the weight, even if they have enough power. Tires will spin pretty easily, even with wheel weights. Plus you need a lot of weight to safely handle a wagon loaded with people going up and down hills. I'd cross a's and b's right of the list for that.
If I'm not mistaken, I believe the H is about 1000 pounds heavier than the c.
I wouldn't go smaller than an H for what you want to do with it. I'd call that entry level for you.
In fact, I'd calculate what you can transport safely, and work backwards from there. Get the most tractor you can.
If you like an H you'll love an M if you can swing it. Always better to go too large than too small.
I think you'll find the prices aren't all that different between the various letter models. They go up a little with size, but shop around and you can get a good deal on anything.
For your needs, I personally would probably take an M over a 300 to save money, and have a little more power. 300's are a great tractor, but being newer will tend to go for a good amount more money.
I think a 400 would probably set you back more than you want to be set back.
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