I don't know Strider's arbitration status and whether he'd a be a Super-2 after the 2023 season, but I would have waited a year on both Strider and Harris before extending.
On Riley and Olson, I think both of those guys may hit the decline button (and perhaps markedly so) midway through their deals. Granted, the low on-going salaries may allow them to be dumped without having to either send money or attach prospects. The thing with both of them is that their power numbers shouldn't completely collapse, but Riley is probably two or three seasons away from full-time DHing.
As some have said, we are painted into a bit of a corner. Team is pretty good if they stay healthy, but there's not much wiggle room (or at least there doesn't appear to be).
Strider had all of 2 1/3 innings in 2021. He wouldn't have gone to arbitration until after 2024.
Harris was a brilliant extension imo. At the time he signed his deal he was set to hit free agency after 2028. However that would have gotten bumped to 2027 after he won ROY. Have to think had we waited his price would of gone up. ROY under his belt and a year closer to FA.