Most Orioles fans are stupid. You don't even realize that the reason the team lost for 14 consecutive seasons was because Angelos refused to let them rebuild and kept trying to compete with the Yankees and Red Sox year in and year out. The first half of that losing streak the Orioles were still amongst the top few teams in terms of payroll. They just never built enough home-grown talent for a core to win with. Finally Angelos ceded meaningful control of the team to MacPhail to allow an actual rebuild. You were probably with the majority of fans who were mad at MacPhail for trading away the team's best player at the time (Bedard). The pieces from that trade alone formed much of the core that ended the losing streak.
If you can't extend Machado, he should be traded. The longer you wait, the less value he brings back. I don't see the Orioles contending for a World Series before he hits free agency without an extension. Keith Law just ranked the Orioles farm system 27th in baseball, and frankly, that might be generous. The wave of talent it will take to build the next good Orioles team isn't even in the system yet. I highly doubt Chris Davis will be a valuable contributor to that team, so there's really no reason to pay him a big pile of money. If you were going to spend that, I'd have spent it on Heyward, who's young, and working on a Machado extension. As it is, the rebuild probably has to come sooner or later, and the only tradeable assets in the organization are Machado and Jones. Maybe Britton.