Hi Cloggy, We need to get a pic of that troublesome bolt and of the 'flared' "tenants improvement" of the bearing holder, as both those (left and right hand) have to come off with their adjustment screw.
Having a look at the cylinder reel, it sure has had a hard life, the wavy blade may need to be replaced....the engineer who does the spin-grind will advise you on that issue.
Seeing the condition of the reel, my advice would be to replace all bearings, as you don't wish to pull it all apart again after it has been restored, just to replace a failed bearing.
Re: the woodruff key and the bearing holder bolt, there is an Illustrated Parts List for your machine in the Parts Lists and Manuals area....this will come in handy to identify any of the parts you need....Access is by subscription, just click "My Stuff" in the top toolbar above, scroll to the bottom of the list and click "Subscriptions", Easy-Peasy!

Instructions for access Click
HERE For the front roller and frame removal:
(1) Remove the bolts securing the frame to the chassis; (1 each side)
(2) Remove the height adjuster by unscrewing the large knob, remove the spring, undo the nut on the inside of the front roller frame and remove the arm.
(3) Slide the complete roller assembly out.
(4) Remove the 2 rubber catcher support blocks.
For the rear roller removal:
(1) Remove the roller clutch cable and adjusting screw from the chassis bracket and actuating arm.
(2) Remove the large roller clutch sprocket by removing the centre bolt.
(3) Remove the secondary sprocket.
(4) Remove the primary chain adjuster. (Black plastic bracket that slides to adjust chain)
(5) Remove the roller clutch adjuster bracket and clutch plate.
(6) Remove the 3 bearing holder nuts and bolts from each side; then roll the roller out.
(7) Remove the 4 (2 each side) lower handle attachment nuts and bolts and remove the handle assembly.

You now have a bare chassis!
Can you please post some pics and report back when completed.