If you're gonna keep trading up, trading picks for players, paying top tier FAs what the market commands, then you're not gonna have any ammo left for a splashy off season. I'd say Pace did about as well as he could with what he had, though if Montgomery's critics turn out to be right then that will be on him. He dumped a POS kicker he over-paid, but at least he tried to rectify his mistake. Also, having a coordinator who is so good he gets poached is not the sort of thing you deserve to be criticized for.
To me a bad off season was in 2007 when, after being humiliated in the superbowl, Angelo managed to retain some defensive starters but otherwise just seemed to be throwing in the towel. The Bears proceeded to go 7-9. There is no way this team implodes like that.
The Bears' biggest weakness last year was special teams. Pace drafted a bunch of athletic kids who can plug in there, and went out and traded for the best kicker he could find who wouldn't break the bank. I know everyone expected him to somehow get Gould but that was always a foolish strategy imo.
My best guess is the 2019 Bears have a worse regular season record but win at least one play off game, which is one more than Fox will compete in this year.