Using the strap over and over again can can wear out the strap and make it less secure over time. Plus at high speeds the strap is not strong enough to handle high wind speeds.

Yes, HEADLOK was created for this very problem. If it has a button on top then HEADLOK can carry it.

Carrying a backpack can be cumbersome and for short rides a backpack is not needed just to carry a hat.

No, HEADLOK was designed so your favorite hat would not be damaged at all when attached. HEADLOK uses the button on top to secure the hat. There is no clamping, pinching or crushing applied to the hat.