Is there a way to update the name database so the names are more in this century than the 1950's?

Yes, there is a FirstNames.txt file and LastNames.txt file you can edit if you wish.

Quick question, is there a reason the surnames in the LastNames.txt seem to be mostly repeated three times or more? Is that for some kind of weighting purpose?

Also, do names have to be added in alphabetical order?

Yes, that's for weighting... based loosely on 2010 census. They don't have to be in any particular order.