The transmissions on thess tractors are not synchromeshed, so they tend to be a little noisy anyway.
You may have a problem, but try this first. You'll need a helper, who need not have any mechanical knowledge or aptitude. Start the tractor with the PTO engaged. With the tractor running step on the clutch for several seconds. Have your helper tell you whether or not the PTO shaft is turning. If it is, try slipping or grinding it into gear. No need to move the tractor. If the PTO was turning, it should stop once you have the tractor in gear and not moving. Then slip the tractor back out of gear with the PTO till engaged. It may or may not start turning again.
As I said, you would normally have to hold the clutch down for a fewswconds to get it into gerar from a stop without grinding anyway. That's to give the shaft time to spin down to a stop. If the PTO is turning pretty freely, though, a good chance that your pilot bushing is gummed up. The front of the driveshaft is held on center by that bushing and as it accumulates gunk, it can bind enough to keep the shaft spinning some, thopugh not with any power to it, just enough to make the gears turn and be noisy as you shift into gear.
That said, it wouldn't hurt to check the freeplay on your lutch pedal, just to make sure it's releasing enough. Free play should be as close to 1-7/16" as you can get it, measured from the front ege of the deck. Adjustment is made with the clevis at the front of the rod you'll find lower down on the pedal arm.
If adjusting the freeplay doesn't fix it or at least make it better, it will almost certainly be the pilot bushing. If you can live with it, I'd wait until I had another reason to split the tractor, as that is required to get to that bushing. It's nested in the center of the rear of the crankshaft.
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