So of course I had to look into this ...
Pulled down from FanGraphs all teams since 1901, a total of 2,646 in the AL and NL only.
Isolated two types of teams: all with with good pitching (better than 95 ERA-) and below average hitting (less than 95 wRC+), and those teams with below average pitching (worse than 105 ERA-) and good hitting (better than 105 wRC+).
Of total teams, there are 288 in the first category and only 50 in the second. It's apparently a lot less likely to have good hitting with pitching worse than 105 ERA-, than it is to have bad hitting with pitching better than 95 ERA-.
Anyhow, here's how it comes out:
288 teams with good pitching and bad hitting: record of 23,380-21,338 = .523 WPCT
50 teams with bad pitching and good hitting: record of 3,728-3,589 = .509 WPCT
So it appears your hypothesis has some merit to it!