Do you know if I can switch from an initial 8-ride later to Monthly pass on Clipper? Thanks.
The answer - generally, is no. The question isn't completely specified - does he want to switch to a Monthly the same month, or in a future month. Definitely you cannot apply 8 rides towards a Monthly pass. But this brings up something that has been a huge annoyance for me in the past, and in fact currently.
In December, I was out of town for a week or two. Add in some days where I rode to work, and I was only going to get say 60% value out of a Monthly Pass vs. just buying 8 rides. So I autoloaded some 8 rides on my Clipper Card and started tagging on and tagging off.
In the past, I would do this with paper tickets. When the month ended, if I had extra rides on my 8 ride ticket, I would usually give them away to a friend, but there was also always a secondary market for 8 ride tickets on Craig's List.
Now, as January began and I had a couple of eight rides left, if I wanted to go with a pass, I would basically forfeit the 8 ride tickets. The 8 rides expire in 60 days. If I bought a pass, I would need my card and the 8 rides would basically be unusable.
The only way out that I can see is to get a brand new Clipper Card, load the pass onto it, and give away the old card (after disconnecting it from my Credit Card). This certainly is not the intent of the system.
To me, the perfect setup is to just charge cash, but give graduated discounts as the month progresses, incenting riders to ride more often and get the volume discounts, without them having to figure out how to keep from getting gamed by the system.
As it is, I am in 8 ride ticket hell for now and am thus incented to ride as little as possible! Especially once I zero out my 8 rides and must then pay cash for the rest of the month, lest I start up another 8 ride ticket. Aside from Caltrain getting less money, in theory every time someone who holds a pass rides "for free", we all "win" by getting cars off the road/less pollution. Every rider - even after they stop contributing additional funds, means Caltrain "earned" something towards their overall utility function.
Lord only knows what would happen if I did buy a February Monthly Pass and tried to validate it by tagging on/tagging off, with 8 rides still valid on my card. The system checks to see if the user has a valid 8 ride or Monthly Pass - what does it do if you have both . I wouldn't be surprised if it caused a Segmentation Fault and took the whole system down. Fun for the whole family.