As far as cropdusting goes it is not that easy to get into as stated above. I talked with a few guys who had to do a season mixing chemicals and loading the plane before they ever got a chance to fly. Not to mention most of those guys are on the road alot.
If you have your tailwheel and around 300-500 hours I would give Van Wagners down in KHWO a call. They fly some souped up cubs and I think they start you out at about 20 bucks and hour and pay for your housing while your one the road. I was told to expect about 500 hours a season (by someone who flew their the previous year). If anyone tries to tell you they want you to pay for your training, walk away. Would have loved to done that but was offered something better before I went down south.
Stay away from this place!!!
http://www.aerialmessages.com/
Here are some of his exploits!!
http://www.ripoffreport.com/reports/ripoff57824.htm