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I have noticed it while running ~/bin/some_command. The ~ doesn't echo until I also type the /. It doesn't cause any misbehavior because there is no binding for ~/ but can be slightly surprising.
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I find it odd that you would have commands in ~/bin but not have it be the highest priority in your PATH. I use ~/.local/bin, but would never type it because i wouldn't have bins that overlap shell commands and no other path would have priority.
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Usually, it is. IIRC, this was when I was just setting up my environment on a new host, after I had populated ~/bin but before I restarted my shell to pick up PATH modifications.
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