I think next year could be a fun offseason. Seattle had a fun blueprint that the Bears could follow. They turned the 21st overall pick into 6 picks (4 in the first 4 rounds). Pace should be pretty confident in his ability to draft at this point. 2015 Pace played it safe. 2016, was quantity approach. 2017 was quality. 2018 was quantity/quality mix as he didn't trade down early for extra picks but did trade a future pick for a 2018 pick. 2019 was neither because of the necessary Mack trade.
If the Raiders are bad again, that 2nd round pick will be in the top 40. That pick will be in the sweet spot as there were 7 trade ups this year for teams between 35-50. Any trade down more than 7-8 picks in the 2nd, typically yields a 3rd. They could then trade down a little there and get a 4th. 2020 looks like a great class on paper. The Bears can turn two 2s and a 4th into picks at say.......50, 64 (see what i did there?), 80, 115, 130, along with those multiple 5th/6ths.
The Bears only lost 3 starters this offseason (Amos, Howard, Callahan), and stand to lose 3 next year, assuming Whitehair re-signs. But they are in trouble depth wise for 2020. No backup QB, all the backup OL that has actually played up to this point, 3rd edge rusher, DL depth potentially gone, and there's only Eddie Jackson at safety in 2020. And like OP said, not a lot of money, even after cuts. So a quantity approach to the draft would probably be an ideal scenario next year.