Jacobs is certainly harder than Garburn. It's only the top rocky part I cannot do on Garburn (Kentmere side) yet I've got nowhere near clearing Jacobs. I always mess up the first bit, even though it's quite possible. The second part, up to the gate relatively easy and then it kicks up which is a killer when your lungs are inside out but it's still do able. It's the steep part after that which I just cannot imagine getting anywhere close to cleaning. Even with the flat bit before hand which gives you a good breather.
As for the person that mentioned a race on Bridleways is illegal, you are right. But who needs to time such an event? The challenge is to get to the top, or at least as far as possible, and thus I believe such an event might be considered legal?