Our first TT was 20' and was towed by a reg. cab truck. No problem driving up and down the lanes in a crowded Walmart parking lot. Could easily park in two end to end stalls in a parking lot. I would say if you can't do this, your TT is not "small". :) Small has advantages.
Now with a 29' TT and extended cab truck, I have to park waaay far away at the back of parking lot and need to straddle something like 20 stalls. Have to walk a long way to the store entrance (bummer). :( 'Course, there's times when you can't find a section of empty stalls you can straddle and you are SOL on picking up food for the CG. :(