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The advice that Farmall Boy posts is well worth remembering. Good tires (short bar 1/2-3/4" in the center with a sharp front edge and laid back with a nice road wear) can make a lot of difference. So can balancing (weighing) your tractor correctly and picking the right path down the track. How much will it cost? It all depends how much work you do yourself, what parts you can scrounge, favors owed to you and access to machinery. The middle of the road solution is to machine the block for 4 1/4" or 4 3/8" sleeves and pistons. That will give you either 340 cubes or 360 cubes. The wrist pin ends of the rods will have to be bushed smaller to accommodate the small wrist automotive style wrist pins. You should be able to do this for $2000 with new bearings and gaskets assuming there aren't any real problems with the rest of the engine. If you budget can afford it a 1650 cam or have your cam reground will be a big improvement over the original cam. Find a 1650 original manifold set (better flow and larger carb mounting pattern) while your at it. If you keep your compression down to where you can run regular gas 80+ horsepower should not be a problem. Another way would be lots of compression and running racing gas. A 1650 head with M&W 3 7/8 pop up pistons machined to clear along with the better cam, carb, manifold set and added rpm will also get you there. There are a few other paths. A lot depends on what you are allowed and how you want to do it. A.P.
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