I see on Aceman's site that there are sometimes challengers that are something like, 50K + H. I went into the ranking system and found that it means Hospitality, and that one is awarded more points per win. Why is this?

I'm not The Boiled Egg, so I might not be entirely accurate here ;) , but my guess is that these 50K tournaments that offer housing attract stronger draws than 50K tournaments that dont. Because of the stiffer competition, you get more points with each win.

Well, because money is spent by the tournament to provide housing, they are putting more money into the tournament, and therefore the WTA rewards them by making them worth more points, which ergo attracts a better field.

yep its Hospitality, Meals at some events

the thing is the higher ranked players can afford the housing and don't need it, yet the ones who suffer are the lower ranked players who really need it more. :help:
Catch 22 :o