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I vote that it's worth fixing and then you'll know what you have. I'm ok with re-using bearings on a case by case basis. You'll have to clean each one and then examine it. Any roughness, or pitted balls and they get replaced. In the top photo it looks like the pilot bearing may have let go. I see something that looks like the back of the bearing cage or part of a snap ring. That would be the first suspect. I'm with Jim in the the ring and pinion wear looks to have been a while in the making. Looks like it's loading at the heal of the teeth and chipping off bits of the ring gear and chewing on the pinion. Could be related since the pilot bearing locates the front of the mainshaft. The trash in the oil gallery looks normal. Stuff accumulates from people grinding gears etc. I get a package of small rare earth magnets from the hardware store and put one or two on each side and also in the bottom of trans and final case area to hold bits of metal that get worn off. The damage to the trans gears happened in seconds so there wasn't really time for the debris to circulate through the rest of the trans. The ring and pinion may have been making metal for a longer time but most of that is likely in the bottom of the case. A second tractor for parts is not a bad idea if you can locate one close and at the right price.
Otherwise, the gears seem to show up on flea bay pretty regularly. Prices all over the place so shop around. Ideally you want the top and bottom to come from same trans. A second tractor would also give you extra pto and hydraulic parts just in case. The rest of it doesn't look bad at all. Like others have said, you could spend four times the money on a new machine and not have half the tractor. I would fix it and keep plugging away.
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