I didn't use the headset with the normal strap for more than a couple hours, but it wasn't too bad iirc. You'll definitely want to get the elite strap at some point tho
In no particular order, here's a list of fun anime to start out with
Fullmetal alchemist brotherhood
Stein's Gate
Death note
Re zero
Konosuba
Sword art online
My hero academia
Miss Kobayashi's dragon maid
No game no life
Attack on titan
Tokyo ghoul