I've been trapped in a co-dependent relationship with San Francisco's Muniserable for the last nine years. ($2 fare, $62/$72 monthly.) When I was a freelancer, and a not-very-successful one at that, I almost always went ride-by-ride. Now that I'm full time, I use commuter benefits to get my Clipper card filled automagically and pre-tax -- so I save about $300 on taxes for the $1,200 I spend on transit. But even besides the savings, I now find the unlimited option is worth it for the emotional security of just knowing that I can nonchalantly approach fare gates and my pass-waving panache won't be rudely interrupted by a red buzzer. Because I am vain.