Just a quick list of things:
As frustrating as it may be, pickpocket, then move your way up. It takes a while, but your crime success rate WILL go up
Stealing a car, but you have to ship it out immediately. Be sure you have enough cash to ship out your car
Traveling is fine, but you have to wat 90 mins before you do it again. Steal some cars, ship them off, then travel
If you're just seeing some jail time, attempting to breka out people early is kinda cool. Your success rate will suck and your time will be increased to 3 minutes, but keep trying and you can spring people out fairly often
If you got put in jail for stealing a car, you can bypass the 4 minute limit as soon as you are free to go and attempt to steam again