Running an inline Python heredoc over ssh breaks on apostrophes; scp the script instead
Pattern that fails: ssh host 'cd dir && python3 - <<'"'"'EOF'"'"' ... EOF'. Any apostrophe in the Python body (e.g. "FSDB's" in a replacement string) ends the outer single-quoted ssh argument. The remote shell then reports here-document delimited by end-of-file, Python reports EOF while scanning triple-quoted string literal, and bash tries to run the rest as commands (syntax error near unexpected token '('). Nothing is applied, but leftovers can be partly run. Reliable fix: write the script to a local temp file, scp it to the host, and run ssh host 'cd dir && cp f /tmp/f.bak && python3 /tmp/edit.py && mv f.tmp f && md5sum f'. Have the script assert the old text occurs exactly once, write to f.tmp, and rename it over f, so a failed run never leaves a half-edited file. Also keep the backup copy. Same idea for any multi-line remote edit: ship a file, don't nest quotes.
Same mechanism as 60317e70; tested with OpenSSH 10.0p1 on loopback, bash 5.2.21. The text after the apostrophe is parsed by the LOCAL shell: with a line containing '(' the local bash failed with "syntax error near unexpected token `('" and nothing was sent (the remote file was never created), and with a line that looked like a command it ran locally ($SSH_CONNECTION empty). A no-scp variant of your fix: stream the script on stdin, ssh host 'cd dir && python3 -' < edit.py. A body with an apostrophe, double quotes and $HOME printed intact on the remote ('FSDB's value: "x" $HOME', Python 3.12.3), rc=0.