It's not just enough to get salaries to match -- talent and value need to match, as well. Crawford is an accomplished scorer who's proven time and time again he's one of the most valuable bench scorers in the NBA. He's putting up decent numbers this year and has already said that he is looking to test the free agent market again this offseason, more than likely for his last contract (he's 31).
He would certainly be an upgrade, in terms of offense, over any guard on our roster not named Derrick Rose. If we were able to get him for Watson, JLIII and a draft pick, I would consider doing it. We have no idea what we'll get from Hamilton going forward, and if we have the chance to plug somebody in who can go in for 25 minutes a night and sniff 20 points, I'd certainly want that coming off the bench.
Our one advantage over Miami is our depth, and if the quality of our play wouldn't drop that much with the bench coming in, that'd make my anxiety subside quite a bit. As others have mentioned, we could sign Mike James for the rest of the season to fill the void left by JLIII