Because web of trust has a weighted system it is best to outsource workers, give them a list of say 300 sites, then get them to rate them a couple a day for a month, or at least until they get up to a silver level. This is the easiest level to reach with a decent amount of power as long as the ratings grow at a reasonable rate.
Supposedly web of trust has an algorithm that assigns a trust rating to your account. So if you rate sites the same way that others rate them then you get more trust, also the amount of ratings you do a day affect your rating.
It is easy to outsource just make them give you the account names that they have created, you join the web of trust and lookup their profiles and ensure they have done the rankings for you...