If you're planning to go F01_RockAndRoll_by-Iltigo, F02_RockAndRoll_by-Iltigo, F03_RockAndRoll_by-Iltigo and so on, please don't. It's a bad habit of Snipe and El-brujo to come up with one name and then just add successive numbers to that name for the rest of their maps. Be more original with your map names - please. :/
We also generally don't like races with no respawn. People don't want to wait around for 3 minutes while people complete a race if they join late. Why not let them race too? Anyway, we routinely add respawn to maps that lack it, so if you don't add it, we probably will.

One important thing if you are thinking of letting some people race and some people not, is that it's best to give people the choice. Some people just want to race all the time, so don't force them into something they don't want. People's mood might also change, so some days they might want to DM, others not. Rao got a Cops'n'Robbers map deleted recently because it forced some people to be cops.
An unfair start isn't a big problem, so long as it's not like some people get a one minute headstart.

In my oppinion a little unfair start is far better than a cluster start, so don't worry about it too much.
As for whether a map that is hard on purpose can be accepted - sure. I am guessing you don't want to add a lot of repairers? So long as there are repairers available after the start, should any clustering occur, I don't see a problem with a repairer-scarce map - so long as you only die through your own clumsiness, that is. I do, however, think that you should have enough health to bump into one or two walls without being unable to complete the race.
Hope this answers your questions.