Some Thoughts:
Front Office
I’ll lead with the obvious, Howie needs to go.  His big win since 2016 was unloading Maxwell’s contract and trading up to be able to draft Wentz.  That’s hugely important and Wentz outstanding play in 2017 directly led to the Super Bowl win.
But…, the list of successes outside that is much shorter than the list of failures, such as:
The Trades:
- The trade of a 4th for Jay Ajayi gets overlooked because he contributed to the SB win, but it’s still not a smart move.  They  gambled they’d get a comp pick at a similar level, but nobody signed him so they burned a 4th and pick for half a season of play.  The fact that a long shot bet came off doesn’t mean it was a smart bet.
			 
- Ditto for Golden Tate.  They did get a 4th back for him, but traded a 3rd (wtf!).  Cost was too high, and despite what they said, there was clearly no plan to integrate him into the O.
			 
- Trading next year’s 4th for Genard Avery.  Exactly one game so far where he has made a contribution.
			 
The string of “smartest guy in the room” decisions and evaluation failures:
- Trading up for Dillard to snipe the Texans now looks like a failure, taking Reagor over Jefferson this year seems ridiculous given how well Jefferson has played.  I like Reagor and think he can still do well, but clearly the evaluation of “fit” or that Jefferson was just a slot WR was monumentally incorrect.
			 
- Nickell Robey-Coleman is a top 5 nickel CB.  Not the most impactful decision, but a great example of Howie thinking he knows better than the rest of the league and patting himself on the back.
			 
- Jalen Hurts picks this year, when DB, DL, LB and WR talent were still desperately needed.
			 
Bad Contract Extensions / Signings:
- Extending Alshon and guaranteeing salary, everyone understands this one enough said.  Alshon couldn’t stay healthy when he was young, what was the expectation here?
			 
- Javon Hargreave has been mostly invisible so far, Malik Jackson has had a couple of nice games, Cox hasn’t looked like an elite player since 2018 (the elite moments like the strip sack last week are coming further and further apart).  In summary we have $40m per year invested in DT and the results are not there.
			 
- Brandon Brooks - a guy who was approaching 30 and had major injuries to finish 2 previous seasons.  It went under the radar because it happened late both years, then he got injured in preseason.  He’s 30, the 4th highest paid OG in the league (per year basis) and he’s on the team until 22 or 23 based on dead money.
			 
- Bringing JP back was an evaluation mistake, because he’s mostly played poorly, but giving him a pay raise to play LT compounds this mistake.
			 
The list of players outperforming their contracts is short, the list of guys not playing up to their salaries is way too long and will take a couple of years to turn over.
Looking at all the above, I simply don’t trust Howie to wisely use an early draft choice or rebuild the roster based on the hole he’s dug.
Coaching
I think it’s been shown over the last couple of years that Doug’s strengths align with being an “executive” style HC, rather than being deeply involved in scheme and play calling.  He doesn’t seem to have the self awareness to understand this though, and the team is suffering because of it.
My indicator for good coaching has always been seeing players asked to do things they’re good at and avoiding areas where they’re weak, and we just don’t see that from this offensive scheme.
I think Doug’s path to future success is to step back from deep day to day involvement in the scheme and play calling, but it’s not something that can be forced on him from above or it will fail spectacularly.  That may be what happened this year, with him being forced to fire Groh (and Watch).   The new batch of offensive assistants have clearly not added anything positive.  Marty Morhinweg?  Really?
If Doug isn’t not just willing, but motivated to make these changes, and bring in some fresh offensive ideas and loosen his control, then he should go as well.
Press Taylor, is it just me, or do things look worse the longer he coaches Carson and more responsibility he has?  Given how consistently Wentz has been making the same mistakes and how his accuracy has declined this year I don’t think he’s being coached well at a position coach level, and I don’t think Taylor is doing much as pass game coordinator to resolve the problems we are consistently seeing this year.
Overall there seems to be a lack of accountability with assistant coaches and veteran players, and a lack of willingness to adjust the scheme to reflect the injury situation and players strengths and weaknesses.
That said, where I think Howie is well below par since 2017, Doug has his issues, but there are still strengths to work with, if he can recognise his weaknesses and is willing to make the necessary changes.
QB Play
Wentz was an elite player in 2017 but has declined since.  The stretches of play where he elevates the team were inconsistent in 2018/9 but still there often enough that I thought 2017 form was just around the corner if the weapons were better, or with a bit more time to recover from the injuries.
Instead he’s gone off a cliff in 2020.  There have been accuracy issues but the most alarming to me is the consistently reckless decisions with ball security, both throwing and with the ball in hand and with holding the ball far too long   I’m honestly not sure how to reset him in season.
Based on contract he’s here for a while, and given that we have seen elite play from him in the past, and very good play as recently as last season, I want to see Wentz with some different coaching.  That could be new position coach / OC with Pederson as HC, or a complete coaching turnover.