As with any trade, practice makes perfect. I was constantly learning more about locks from the Internet, and learning more about how locks actually pick, and that, combined with actual practice, soon cut my average time down to less than 60 seconds per machine.
Stubborn locks? I'd just move on
I also learned to pick padlocks that were used to lock up the machines. Yes, there were some locks that would give me trouble, but I soon realized that rather than spend five minutes adjusting the tool tension to match the lock, I could drive down the street to a different machine and have that one open in 30 seconds.
With practice and increasing expertise, I started to work on a schedule. Three days a week, I would leave home, drive for a hundred miles or so, and visit a new town. I would stick around long enough to make $500 to $1,000, and then head home. This would be about 10 machines, on average. Not much work at all.
Preference for older machines
I did develop a liking for smaller towns (population 15,000 to 80,000). In the larger towns, there are enough newer vending machines with unpickable locks. While there may be a lot of older machines in larger towns, finding them can take a lot of work.
My normal routine was to get off the interstate and look for a tourist information booth. I would get a city map, and ask about the locations of hospitals, colleges, hotels, and any other large public areas such as malls, bowling alleys and zoos.
I would then go visit a few different places. If they all had newer locks, I would get back on the interstate and proceed elsewhere.
Learning the best hours
I soon developed routines I would do while visiting these towns. Hotels were visited during the afternoon hours. Hospitals were early evening (8 p.m., when visiting hours were just about over). Colleges were sometimes open till midnight, but before 10 p.m. seems to be the best time. Colleges and hospitals were also pretty clear at 6 to 7 a.m.
If a town was going really well, I might get a room at a local hotel and spend the night, and resume looking the next day.
One nice feature of some larger buildings was multiple machines keyed alike. I could spend 30 seconds picking one lock, tighten the tension on my pick, and then go from machine to machine just like I owned a key, simply open it and grab the money.
I rarely took the change from a machine. Change makes a lot of noise when being poured out of a metal bin. It also extends the time with the machine open. If I just took the bills from the bill holder, the machine would be open less than 20 seconds, thus severely limiting the opportunity someone would see me in the machine.
The day my luck ran out
Well, I guess I knew it would happen sooner or later. I was at a college in the Midwest, and before proceeding to the main lounge, which held about 10 machines, I decided to check the tension on my pick by testing it on a machine in a different building.
I didn't have the pick out for more than four seconds before the machine opened, and I was not about to close a machine before taking the money out. Through the door next to me walked not just anyone, but the manager of the college physical plant building, who happened to know who serviced the local machines. Which was not me.
He followed me across the campus and radioed the campus security patrol, who reported me to the local police force. I managed to drop my tool into a bush, but I was nonetheless charged with and convicted of theft.
First fine: $200, hardly a deterrent
I was fined a grand total of $200. That certainly wasn't much of a deterrent for someone making well over a thousand dollars a week, working about six hours.
Several months later, I made another mistake. The day I sprayed Teflon on my tool to help lubricate it, I was in a lounge near my home. I walked up to the cigarette machine, and within 20 seconds, I had $90 in my pocket. But because the tool was so loose, I was unable to relock the machine.
Another unlucky day, or so I thought
As I stood there for a minute trying to relock it, one of the lounge employees saw me poking at the machine. The employees called the police and reported me.