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bpo-16806 introduced a regression with the following change:
commit 995d9b92979768125ced4da3a56f755bcdf80f6e (refs/bisect/bad)
Author: Anthony Sottile <asottile@umich.edu>
Date: Sat Jan 12 20:05:13 2019 -0800
 bpo-16806: Fix `lineno` and `col_offset` for multi-line string tokens (GH-10021)
get-pip.py does now crash:
$ ./python get-pip.py --help
python: Parser/parsetok.c:266: parsetok: Assertion `(intptr_t)(int)(a - line_start) == (a - line_start)' failed.
Aborted (core dumped)
Python 3.8 is also affected.
get-pip.py comes from: https://bootstrap.pypa.io/get-pip.py
Reproducing depends if REALLOC() returns a new pointer, see below.
I attached get-pip2.py: simplified version which crash when using "./python get-pip2.py --help". If it doesn't crash, duplicate lines to make the file larger.
--
The root issue seems to be that tok->multi_line_start isn't updated on REALLOC() in tok_nextc():
 newbuf = (char *)PyMem_REALLOC(newbuf,
 newsize);
 if (newbuf == NULL) {
 tok->done = E_NOMEM;
 tok->cur = tok->inp;
 return EOF;
 }
 tok->buf = newbuf;
 tok->cur = tok->buf + cur;
 tok->line_start = tok->cur;
I guess that multi_line_start should also be updated there?
 tok->multi_line_start = tok->cur;