Jim
Here comes some theory from a
Numbtie if a string is stretched between two fixed points and returned to the same fixed points, it should have the exact same tension on it
B U T ———
If the roller at the headstock is slightly oval, ( like a rugby ball for instance ), when it moves with the string it could return to a slightly different position and that could be stretching the string enough to make it sound slightly sharp.
I know your method of making the rollers is limited and they cannot be completely accurate, as they are “ hand turned” on an electric drill or filed, it’s a long shot but it could possibly be an answer to your problem.
As I mentioned in my opening statement.
THIS is only some theory from a
NUMBTIE but it may be the answer to your problem, so try another roller and measure it with a micrometer if you can, then check the old one to see if there is any discrepancy between them, OR
if it cures the problem just sit on your

and play the beast!
I hope this helps, as it’s the best I can come up with this early in the morning!
Cheers
Robert