Anecdote related to me on Caltrain today.
A rider I know got his brand new Clipper Card. He set up autoload for 8 ride passes, and put $5 in cash onto his card, per instructions from Clipper, that you need to have at least $1.25 in cash in order to use your 8 rides. This is because (insert broken record) the system deducts the full fare for the longest trip possible, and refunds you when you tag off.
He tagged on this AM in San Francisco, and Clipper charged him $12.50 - the fare to Gilroy. In Mountain View, he forgot to tag off. Had he tagged off, the $12.50 would be refunded, and he would have one of his 8 rides deducted. Since he forgot, he was not refunded, and his cash balance went to negative $7.50.
That evening, when he tried to tag on - he saw "TRAVEL INVALID". This was because he didn't have "at least $1.25 in cash on his card". With no Clipper Kiosks on the platform, he was forced to add value online - and wait 3-5 days for that cash to appear on his card, before he could use his 8 ride tickets.
His only option was to buy a 1 way paper ticket from the machines. Well, not his only option, he basically bullshitted the conductor into letting him on (The conductor's reader was broken anyway), but his card is dead unless he finds a live kiosk or waits 3-5 days.
The High Value Ticket would prevent this problem.