Novice here, but determined. I don't own a car living in the city of Chicago, so i've had to rent cars for my two pins both of which I got just this year. The first one wasn't far outside the city, but for the second one I drove 380 round trip miles to Appleton, WI to pick up my Black Knight project machine. In Chicago, renting a car at a reasonable price means first taking the 45 minute trip on public transit out to O'Hare Airport, then tracking down and waiting for the Hertz shuttle to the rental car lot. Then once the pin pickup is complete, driving home to quickly drop the pin off before turning around and heading all the way back out to the airport to drop off the car, THEN finally returning back home on public transit again.
That happened to be the weekend after Midwest Gaming Classic, so two consecutive weekends of getting to pick up some New Glarus brews at the Mars Cheese Castle made the trip all the more justified!