From a business point of view, I know where I have been (and not going back!) and I know where I want to be - Threads like this help me determine my path or paths I take.
I have thought about the $99 up-sell route but looked at it as a bait and switch so I decided not to do it. Ads in the paper are $99-$129 for a single story, I could match that if the house was 800-900 SF and everything else is going to be higher.
If I had four 2 man crews washing 4 houses a day each, @$99 I would end up with less then $25/day in my pocket. Actualy a lot less when you figure in the advertising $$$ needed to get 16 houses a day for the season..
On the other hand, if I had a "real" job and just needed extra cash for fun money, $50+/hour looks real good.
The $99 guys will always be around but with different faces as they replace themselves.