Caltrain's implementation of Clipper is just a total wreck. They should go on the same route as Golden Gate Transit.
Prior to Clipper/TransLink, Golden Gate had two options of paying: cash or discount ride tickets giving riders specific zone coverage (almost like Caltrain), but they didn't have a monthly pass.
When TransLink's pilot program came around, instead of having TL sell multi zone electronic ride books, Golden Gate agreed to only accept electronic cash on the card and give the same percentage discount as their discount paper ride books. This meant no more worrying about expiring ticket books, and buying multiple zone books to cover the zones you ride; it was just simplified. This benefited everyone, including infrequent users and tourists who got a nice discount and incentive to ride GGT and GGF.
Caltrain is just a total mess. Clipper's implementation meant the agency kept the 8-ride tickets with plenty of rules and limitations on how far one can travel. There is also awkward rules on the use of 8-rides and monthly passes that just makes it silly.
Here's a simple suggestion for Caltrain, follow Golden Gate's way:Eliminate the 8-ride tickets and make card users pay Clipper e-cash with the same percentage discount offered on the 8-rides. They could eliminate monthly passes and give the same discount, or modify the rules so a passenger who spends more than a specific amount within a specific time period will automatically "earn" a pass, thereby free rides for the remainder of the month.
Update: I cracked some numbers, the discount for using 8-ride tickets is 15%. By using my idea, all e-cash paying customers w/their Clipper cards automatically gets a 15% ride discount.