I want to thank all of you for your input. Everyone made great points. I think I'm going to take everyone's advice a little here and I have come up with this decision:
You hit the nail on the head.
1) I'm going to start with Five 200 Page sites that I'm interested in.
2) All areas will have a decent number of advertiser dollars and decent amount of people looking for the info.
3) I'm going to just let them passively grow by 1-2 new pages a week.
4) Which ever niches produces the most bang for your buck after say 1 year, I'll go full throttle on those and ramp them up to 1,000 page sites.