Yes, any small block with flat tappet cam and a place for a fuel pump will be a drop in replacement.
Going with a later model is doable, but it won't have the stock appearance, stuck with an electric fuel pump, having to buy an intake and adapt your carb.
The later models also had a different rear main seal, which means a different flywheel. Not sure if it will work with your bell housing and starter, clutch. Chances are you will not find a truck flywheel used.
It gets complicated, if you did this every day and had a shop full of parts to choose from and all the connections, then it would be feasible. Try to keep it simple and within budget.
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Today's Featured Article - Upgrading an Oliver Super 55 Electrical System - by Dennis Hawkins. My old Oliver Super 55 has been just sitting and rusting for several years now. I really hate to see a good tractor being treated that way, but not being able to start it without a 30 minute point filing ritual every time contributed to its demise. If it would just start when I turn the key, then I would use it more often. In addition to a bad case of old age, most of the tractor's original electrical system was simply too unreliable to keep. The main focus of this page is to show how I upgr
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