I would say that as long as the bore that the outer race sits in isn't gouged or cracked and the bearing can sit perpendicular with the shaft when its pressed all the way into its pore, its all good. If any of those gouges on the bottom are high enough, the emery cloth should be enough to take them down and allow the bearing to sit nice and flat down in there. I don't know what the main bearing looks like, so I don't know if this is entirely true or not, but I know that with bearings of that size or larger, sometimes manufacturers put a little groove in the inner or outer race of the bearing to help get the last ball in between the races. Perhaps that could be part of the reason the bearing came apart? But I don't know, those look like pieces of a cage, maybe it didn't. Something else come apart in the motor that could have found its way in there?
As for the oil flow port, I wouldn't be concerned. All of my advice is based on working with 60 Hz rotating equipment. With our equipment, the flow passages designed like those are just there to flow oil through. If any certain level of pressure was involved, or a specific flow rate required, it would be a machined feature rather than a cast feature. Just my thoughts, take em with a grain of salt, I've drank a couple beers this evening lol

good luck with the rebuild. Getting ready to take mine apart in a month or so, hoping I don't have to tear into the bottom end!