Just checking in to give the opinion.
Personally I like Howard. He has limitations in both the receiving game and is far form 'explosive', but he's a hard nosed north-south running back with very good vision. He will rarely go down behind the line of scrimmage, is a respectable blocker when asked to stay in (allowed 2 pressures on 92 pass blocking snaps last year) and rarely fumbles the football (5 fumbles in his career, 3 lost - with 850 touches that's a pretty crazy low percentage (0.59% fumbled 0.38% lost)).
For the Bears he just wasn't a fit. My thoughts are that Nagy wants one RB that can do everything like a Kareem Hunt. Howard is not that guy. The issue I have with that logic is that RB that can do it all is either an expensive FA or a higher draft pick. IMO when you look at teams that win a championship it's typically through RBBC and cheaper contracts, but that's only my opinion. I also see how a Barkley/Elliott completely change how those respective teams perform.
For the Eagles he's going to fill the Ajayi or Blount role. Both of those guys were grinders who lived between the tackles and was an important skill set that vanished when Ajayi went down last year. They patched together some of that production with Josh Adams last season, but late in the season the rookie had a knack for fumbling at the worst time, so his usage vanished in the playoffs.
Finally, when looking at the trade I'm happy as an Eagles fan. A 6th round pick (that can be a 5th) is really nothing and the ~$2M contract won't impact any other moves. Add in that the team will have a few high compensatory picks coming their way (estimated 3rd and 4th rounders) the 5th/6th is not an issue. I'd add if Howard performs well and is healthy in the offseason someone could easily offer him a decent deal, which means another comp pick could be coming to Philly. Thinking this through a good comparable RB is CJ Anderson, who's still hanging around as a FA, but I'd also say he did sign 4 year, $18M deal with Denver a few years ago, so the market is probably somewhere between those two.
The trade for the Bears is a big shrug. I can only assume based on the number of RB draft visits and Howard's usage/production that they weren't going to have Howard on the field much, so they weren't going to do much that would warrant a high compensatory pick anyway. The potential risk there is that if they draft a RB early and ultimately that player isn't ready to produce yet there could be a problem. Just thinking back to last year's draft, which had a higher overall grade for the RB position, in the first 2 rounds there was Saquon Barkley, Rashaad Penny, Sony Michel, Nick Chubb, Ronald Jones, Kerryon Johnson and Derrius Guice. Of the 7 RBs drafted 4 produced right away while the other 3 are a mixed bag of unknowns. After those rounds not a single drafted RB had more than 521 rushing yards (Freeman), so it's fair to assume there's a good chance the 2019 Bears rushing attack will largely feature Davis and Cohen with the potential of a rookie giving some production.