Besides the obvious "gloves are for pussies", gloves will weaken your grip. Like shoes and the dead-lift you wanna have as little material between your skin and the tire for optimal grip.
Just chalk up beforehand to ensure that your hands are dry.
Also, the profile of the tire is flawless, so I don't see any reasons for using a 2X4. If for some reason you do, one will be enough actually. You'd set your grip at an 30-45Â° angle from the block and start flippin'.
Also, remember to warm up your biceps sufficiently and always drive through your hips. If you get stuck, never try to struggle it up with your biceps, that's just asking for a tear.