Well, we're old enough :P
Some copies made with CopyIIPC, needed an additional file, called
NOKEY.COM. Do you remember ? :)
I defeated (ehm...) many protection schemes.
Prolok was hard (I used only DEBUG in those days, no Internet, no
infos...).
Debugging and disassembling was a hard task, since very often the
protecting scheme decrypted its own code with self modifying code,
cleared interrupt table (say hello to your breakpoint :P ), read some
disk areas, decrypted the program itself...
In this case, it's not easy to modify the test instructions (JZ/JE to
JMP) since they're encrypted...
In some circumstances, a TSR was needed, intercepting the read call to
the damaged sector, fooling the program giving back the same damaged
data of the original disk.
When you used Teledisk, did it flagged some error?
Did you copy the entire disk?
Would you send those images to me? I can give a look...