This issue it’s all BALLS and rollers, bearing etc

The attached photo shows a way to save your balls getting dirty and misplaced! As you can see the cut down plastic drinks bottle saved my balls! I had to replace the top cup and cone bearing in my 101 earlier this year, the bottom bearing was OK. A micrometer or a good Vernier caliper is essential to ensure your balls are the right size, in this case ¼ inch or 0.250”, quite easy to confuse with a 6mm ball bearing.
Indians used loose rollers in the motor wheel hubs and gearbox, standard size is 0.2495” NOT 0.250, time to get the micrometer out again! The rollers are somewhat sacrificial and when worn they can take up play in the bearing races by using the next size up (0.250”) only as long the bearing races are not pitted by corrosion or electrolytic reaction due being left stationary too long. It pays to rotate the motor every 6 weeks to prevent this. The electrolytic reaction causes pitting which will destroy the finely finished rollers and races.
It is quite an art and takes a lot of skill to determine the correct roller bearing clearance too little is disastrous. The best information you can refer to is from a Harley Davidson factory manual which clearly explains the process of determining bearing fit.
Strangely Indian used metric sized ball race bearings in some applications like the brake drum on Chiefs. Makes things easy to replace and used a bearing marked 2rs which means 2 rubber seals. In the wheel itself there are caged rollers as in the crank and very prone to corrosion and pitting. If the inner race is unserviceable get a bead of arc weld around it and it will drop out very easily, same trick can be used on steering head bearings.
Indian Chief brake side wheel bearing

Micrometer measurement of a roller at 0.249”
Electronic caliper showing the same roller, very great care is needed with these type of caliper as it’s too easy to incorrectly zero the setting.
Remember:
You always win with Indian Tim 
Next month a tour of the workshop, better get out there and tidy up!