Simply take a playlist you need (animal, surf, skiing or snowboarding) and do one a day. After you have finished these off take any playlist you like, and watch 10+ videos from it remembering that you need to hit 100 by the time you are done.
A good way to avoid having to sit and fast-forward is to simply let a playlist like 'Awesome' (with short videos), run and come back to it in 30 or so minutes. You can even snap the app and let it run on the side for a little bit of time and then close it out for the day. When going for this achievement I would turn the app on when I woke up, and for the hour and a half before I left to go to work I would let it play. Knowing your playlist does not contain long videos is key to being able to step away from the Xbox and not have to fast-forward.