To be honest, that shakespeare looks seriously over priced. Wouldn't touch it, don't reckon it's been well looked after!
Just looked at the pics of that Searider 5.4 and I think I've sussed the problem. It's too far back and therefore too low on the trailer right? No, wait, I'm confused. It needs to be the other way round? Ok, maybe I need lessons in how to tow
I think what you have there is a case of "winch frenzy", where you go "I've got this winch on the font, so I'm going to crank it in as hard as I possible can, don't care if the boat ends up off the rollers". Not helpful!
At least he's got a spare steering wheel on the front of the trailer. No, wait, I've gone again, it's not a steering wheel, it's the weight from a throwline.
Blame my friends, they were the fools who provided me beer...