1. What exactly is "messed up" on the front PTO driveshaft? My similar setup seems to be a flat plate with bore, key, and setscrew to the shaft. Other end is a double-strand roller-chain coupler (essentially coupling 2 parallel sprockets together) to the pump input shaft. This is standard industrial power-transmission stuff typically which may be fixed by a machine shop or a visit to Applied Industrial, Motion Industries, (etc).
2. Waterpump work that I've done on a few of these tractors usually requires an arbor press and some custom pins/pushers to do properly if you don't have the right-sized sockets (usually they can work well inthis application).
3. If the 300 has the older "H" style block with the core-cover on the side of the waterjacket, I would definitely take that off, replace it and the gasket, surgically clean the gasket face and reapply with RTV. The ones I have taken off look Ugglee inside and definitely had restrictions.
4. Have you verified the pulley also turns the waterpump impeller? I had an "H" once which was missing these key pieces. Fan, fanbelt and hub all would turn like mad when running. But the cross-tie to the impeller shaft was lost/missing/discarded and so the impeller never moved. Very fast overheat nearly every time.
5. I think replacing the hoses is also an excellent idea. As is the coolant (sorta by default). The latest tractor I'm working on must have been run on straight water by some cheapo...incredible sludge and rust inside the water jacket.
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