The O's have the worst player in the league, quite literally, being paid $21M/year for the next 4 years after this one. With a stingy owner, there's no chance they spend anything in the free agent market. There's one major route for acquiring talent.
They've basically ignored the foreign market for as long as I can remember. There's another route for acquiring talent.
Of their 7 top 5 picks in the last 20 years, they've hit on 2 that have become anything more than above-average players. One's gone ad one's out the door. They've been notoriously bad at developing any minor league talent. There's another route for acquiring talent.
So now we're left hoping that the Machado trade (and likely subsequent Britton and Schoop trades) alter their course. Not optimistic. Even if they hit on it like they did the Bedard trade, that's one long-term above average player in Jones. Tillman has basically been a roster filler or worse for all but two of his seasons in Baltimore.
I don't disagree with most of what you said (although I think you're underselling Tillman's importance to the team from the later half of 2012 through 2016).
But the team has a chance at a new chapter coming up. For as awful as the Davis contract is (and it still puzzles me who they were bidding against there), Angelos has been much more willing to open up his checkbook in the past several years. They've been an above-average payroll team for a few years now. The payroll nearly doubled between 2011 ($97M) and 2017 ($182M). Moreover, Angelos is ceding more and more control of the franchise over to his children, which is (hopefully) leading to a new era in Orioles history. Hopefully the ownership edict to not spend money on international players will vanish with Peter Angelos. Similarly, the front office should be seeing changes soon. Duquette should be gone this off-season. Brady Anderson is taking increased control of baseball ops even with Duquette still here. The O's front office is a dysfunctional mess right now, no doubt. But there's at least the hope that the younger Angelos' could learn lessons that their father couldn't, and that an empowered Anderson could mold the franchise in ways that a neutered Duquette was never able to.
Don't get me wrong, I'm still pessimistic about their future outlook. But I don't think they're Ottawa Senators level of bad. The Senators have hundreds of millions in debt, traded away a likely lottery pick in 2019, locker room drama, and a front office member on trial for assault. There's even less hope for redemption in Ottawa.