For 3 days now I've been trying to properly flush and re-oil the 4 bearings and 1 roller clutch bearing.

1. How can I tell if a flushed bearing is optimally clean and ready for oil?

2. Is it reasonable to have to re-soak bearings over and over this many times and for this long? Or am I just up my own ass and wasting time?

3. Really I just want to know how to tell what a healthy bearing is as well as be able to tell when a bearing is beyond repair

Monday Night - Soaked bearings for about an hour, some, not much dirt came out. Dried them and applied a drop of hot sauce to them. At this point I thought they were clean and ready to be reassembled. But I noticed one bearing was smooth as butter and seemed to spin for EVER. Wanting the rest of them to spin like the butter one, I decided to soak them again, over night

Tuesday Night - After soaking them in lighter fluid a second time, this time over night, there was 5 times as much dirt. Took them out and set them aside to dry

Wednesday Night - Sure that they were completely dry, none of them were spinning for a particularly long time (Some stopping within 1 second and others within 3) Applied oil. Same thing. Frustrated and scared, I decided to just soak them again

Note - The Shimano Chronarch I am maintaining right now is a 100A and has probably not been thoroughly cleaned in 10 years. I've been doing the basic maintenance but never this deep.

A clean bearing will spin easily and quietly and come to rest gradual not stop suddenly. If they've been neglected for ten years they may be worn out. Can't say for sure with out see them in person.