I think Angelos has actually been much better as of late because he's getting older and realizes that he has no hopes of winning if he doesn't shell out money.
The issue that I really see is two part. 1) Baltimore is a small market team. They aren't the Yankees or Dodgers who have probably damn near $1B to spend in payroll if they really wanted. I think I read somewhere a few years ago that the Orioles have like $200M to spend in payroll a year. I mean, yeah, $200M is A LOT, but when a good starting pitcher gets like $30M a season and an elite positional player can easily match that, $200M can dry up really fast when trying to tool up your roster. 2) The Orioles farm system absolutely blows. I don't know if that's bad drafting or poor development, but the Orioles generally rank in the bottom 5 farm systems in the MLB. That has changed a bit recently, but once Chance Sisco and Austin Hays get called up (likely very soon), the farm system goes back to being absurdly subpar. Plus, whenever the Orioles have a farm system player worth half a damn, they end up trading them for a half year rental. Like, sure, Zach Davies and Eduardo Rodriguez aren't fantastic players, but they'd be doing much more than the current backend starters for the Orioles.