There should be a whisper of chamfer left but not enough to help much. If the rings are gapped properly they should go in with finger work around as the barrels drop down. I have found a few 466 rings way too long, they wouldn't even go into the cylinder to gap.
Block up #2 or #3 around TDC (just a stick the right size under a piston) and carefully work the jugs down to whetre the top ring is about to go in. Push a ring (gap in the right spot) into the groove and wiggle the barrel assembly a bit until i slips in. Then get the other piston's ring in. Move down to the second ring. The thin oil rings are delicate so take it easy there. Once all rings are in drop the barrels a bit and remove the stick, turn the crank and assist the barrels to move down as the 1-4 pistons come up into it. Repeat the ring fiddling insertions. Do 2/3 first so you can work around 1/4 in the much reduced space under the barrels, it's pretty hard to do 2/3 last.
You can use hose clamps as ring compressors. My experience is that in the time it takes to get them on and off I can have the barrels done and down. If you have reservations about doing it with fingers then get the clamps. Just barely tight, and well oiled.