I have come to a conclusion about Pole Position, It doesnt genereate monery. Its just a save point.
Now I can help you with "Messing with the Man" though.
This mission is pretty difficult... and its gonna be pretty difficult to describe how to do it so bare with me.
First of all, you MUST stock up on lots of ammo, specifically shotgun and LOTS of uzi bullets. You can do this by going to ammu-nation or by driving around and finding them.
Now, There is a free missle launcher down by the Vice port Authority, its in a pool in a hotel down there. Its hard to describe exactly where it is but Ill try.
When coming from the first island over the bridge, the first street you come to is the main one, make a left, go all the way down but not to far, if you hit the boatyard, youve gone to far. Theres a street before you enter the shipyard BEFORE the line of condos, make a right on that street... keep going strait and the hotel is on your left after seeing a feild of grass. There should be palm trees n stuff outside, go in through the hotel and theres a pool, BAM.. theres the missle launcher.
Now if that wasnt to confusing(which Im guessing it was.) Your going to need two of them, so do some taxi missions or vigilantes and then come back and get 4 more missles.
Now, with all your ammo and missles for you launcher, you should be able to blow everything out of sight and raise that choas meter really quick. Remember Blowing shit up works best but if you run out of vehicles, which i doubt but it can happen, Just shoot everyone in sight. And after all that! You only get a measly 1 or 2 grand!!!!!!!!!! whooohooo!!!!!!!!!
Hopefully that helped. Sorry the confusing directions but its not easy to describe. You know where to come if you need more help.