I wrote a pretty comprehensive guide for toe rolls in another thread a while ago, here's the link:
The main problems you have are you're throwing your head forward and starting the roll way too early. Wait until you've gotten a nice clean upwards pop before throwing the trick. You want to be aiming to take it straight up and wake to wake, but really tall. This should make progression much easier. To do this; when you pop, push your chest up first, then tuck into the roll.
Your handle position is mostly good through the roll but you're letting it drift to your right front pocket too much, especially on the landing. You should aim to have it touching your right kidney area. Try taking your back hand off to help, or even better imagine you're trying to punch someone behind you, using the hammer part of your fist (the outside of the pinky, keeping the back of your hand up)
Also bend your knees more on your approach. Your right leg is barely bent at all and your left leg should be bent a little bit more than it is. They should be bent the same amount
Finally close you shoulder off to the boat. Your handle should be in your right back pocket, but that doesn't mean you have to open your shoulders to the boat completely to get it there.