There's no evidence that Harolds Club overstamped the roulettes. It was likely done by one of the home or charity users that got hold of the chips after they were removed from the Club.
Yes, some table numbers and colors are worth more. I've been collecting these for over 10 years and still don't have some of them!
For instance, I have no N4204, table 15 roulettes. Maybe Mr. Roulette (JerryB) does, but I've never seen any. And I have table 101 roulettes only in yellow and orange although TCR shows 7 colors are known.
All these chips have a reputation for being common, because some of them are. It would be nice to have the values in the catalog show the scarce ones, but with the numbering system now in use in TCR this may not be possible. I'll send scans of the ones I've found to anyone who would be interested.
Sample page is shown below:
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