I can't help with the band adjustment (haven't done it yet myself), but I know exactly what you're talking about with regard to the rear shaft bearing retainer (sometimes called the seal retainer.)
I assume by 300 you mean 300 Utility and not Farmall 300. If you mean Farmall, I don't know whether what I'm about to say will apply to your situation.
During the past couple of weeks I've removed the rear PTO housing cover from a 300 Utility and a 350 Utility. The 300 had cover # 360153R11 (non-recessed), and the rear shaft bearing retainer popped off easily with just a little prying with a screwdriver.
Not so with the 350. It had cover # 364708R2 which, as you noted, is recessed. I could (just barely) get a screwdriver blade between the outer edge of the rear shaft bearing retainer and the recess in the housing cover, but there wasn't enough room to do any effective twisting or prying. I tried and failed to get some skinny hooks into the bolt holes and behind the retainer so I could pull on it. Finally, I did just what you're describing pound sideways on the bolt holes with a punch. As you know, it's hard to get a good angle on it in order to do that. I did goober up the bolt holes just a little, but the retainer finally came loose.
I'm considering a couple of approaches for reassembly. I was going to drill and tap the retainer for a pair of 5/16 stainless studs to give myself something to pull on next time. I'm currently leaning toward tapping the smooth bolt holes in the retainer with the next largest standard thread (looks like 7/16 or so). This won't interfere with the retainer bolts, but next time I remove those bolts I'll be able to insert some cap screws to pull on, or to screw in (gently, being careful of the existing threads in the cover) to push the retainer away from the cover.
If you're REALLY stuck right now, you could probably try partially tapping those holes with the retainer cover in place. You don't want to go too deep and chew up the retainer bolt threads in the cover, but you could probably create enough threads in the retainer to get a sufficient grip on it. Of course, you'd want to clean the whole thing thoroughly before reassembly to get rid of any chips.
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