I had a lot of fun robbing stores in SR1. My first time playing it, I drove around the city, demanding money from the clerk in every store I found. While I drove around, I was also listening to that hilarious talk-radio station(I was mad that it didn't return in SR2).
Later I figured out how I could rob them after business-hours, and I eventually got that down to a science. I got my favourite SUV, and would park it with the rear just a few feet away from the door of the store. I would then run inside, raid the safe, and I would have the loot stashed in the SUV within 30 seconds of parking. I repeated the process on half a dozen stores, before cashing-in all of it in one shot at the pawn-shop. I made thousands of dollars per night, and quickly unlocked the achievement for it. I thought it was cool that each shop would have police-protection after a few nights of repeated burglary.
After playing SR1 for a few weeks, I noticed how I always saw tractor-trailers on the off-ramps of the highway, but never saw them in town. I decided to hitch a ride on one(which wasn't easy), and ride for a while. To my surprise, the truck continued its journey into the city, and smashed its way through traffic. That was pretty funny. After a while, I fell off the truck, and it vanished as soon as it was off-screen.
In SR2 co-op, my buddy was trying to do all of the races for the achievement, but was having difficulty. I discovered that I was able to eliminate the competing racers, as long as I wasn't participating in the race. I drove in the on-coming direction with my APC, and would hit the nitrous just before the collisions.
In co-op with same friend, we had to repeat one mission half a dozen times because BS kept happening. One such incident was when I detonated a satchel charge, which was part of the mission, and the car I destroyed happened to land on both of us. "THIS SHOULDN'T BE DIFFICULT" is now an inside-joke.