First of all, thanks everyone for your replies.
1) How much is the entry fee? How are Level 1 pre characters supposed to have it at that group photo op in the beginning?
I am assuming anyone that wants to get in on the race will have at least one other character that could give the money in advance. I didn't pick an entry fee, because I don't really know yet what type of people would be interested. If it is a lot of experienced people, they would probably be okay with a higher entry fee with a possible higher payoff at the end. If a broader base wants to enter, the entry fee could be lower. If there are a significant amount of donations, we could probably do away with the entry fee altogether. Basically it is just there to make sure that the winners get something, even if the donations are lacking.
2) Won't this turn into people rushing through pre, having friends and friends' heroes powering them through most everything, and using a few tomes to kill the Doubledoofus? Or is that the intention in the first place?
I don't think there is any way to prevent this from happening, and thus it was part of my initial design consideration that guilds, heroes, tomes, scrolls, etc would be used. I think it's going to take a significant amount of time to complete, regardless.
3) Why doesn't the race finish at Drok's, not Hell's Precipice? You wind up in Drok's after finishing Hell's, not back at the outpost.
You are correct, the race should finish at the location you end up in, not the location you start from. I will change that.
Sounds cool but how can it be judged?
Since the only way to get a protector title is to complete every mission and bonus, if you see a character as level 1 in presearing at one time, and with the title a few hours later, this is verification that they finished the race. Unless a ton of people sign up (which I'm doubting just due to the time requirement), judging who gets to the final town first with the title shouldn't be too hard; additionally, there is the added rule that you should state that you've completed the race in town as soon as you get there, just in case it is an extremely close race.