Take a small paper clip and use an acid brush and squeeze the paper clip in the back end of the acid brush and use that to slide around the lip seal and you will fix it. You can use that as well to install atuo type transmission piston lip seals. Same idea and it does work...
I feel you pain :( You will get there!! You should install grease on the seal lips too. Maybe time to machine a tool that is slip fit over the shaft, so it pushes on the seal lip while also pressing on the face of the seal.. Also, seems like possibly that seal ID is slightly too small? Maybe measure the diameter of the shaft where the seal sits?
In the video, the shaft looks a little rough. Did you dress it up with Emory cloth before trying to install the seals ? If not,do you think that might have helped?
The area where the seal rides was pretty good. But you are correct, light polishing with emery would be fine. But if there is a groove worn in the shaft, you can try and reposition where the seal rides on it by not driving it fully home in the bore. But if there's not enough room to do that, a speedy sleeve might be available.
lol at 2:44 Steve drops the S word, sh1t. Thats nothing compared to the video a few years ago when he went to pick up out board motors from that radio DJ and the guy was handing out endless supplies of the F word.