Has anyone used an Osprey Fairview 36L Wheeled bag as a personal Item on flights?

I am traveling to Europe for a 6-week backpacking trip, and I want to take a few flights to cut down on train time. Most short flights across Europe seem to have crazy price hikes for carry-ons (for someone trying to travel on a budget).

I am aware most airlines have different regulations, but I'm just wondering if anyone's made it work. The flights are so short that I am not worried about legroom either. Anything to save a few hundred dollars.

Any thoughts? Travel hacks for carry-on prices? Advice? TIA!