85 and 87, the newer generation of freeways in the San Jose area, do have odd control city choices. While Mtn View and Gilroy are definitely accurate for 85, it is odd since most bypasses (nationally) have long distance controls. So at the southern 101/85 jct, I'd expect 101 to have a San Jose control and 85 to have a SF control, but since 101 has always had the SF control and 85 is a much newer highway they decided to give 85 the local control of Mtn View instead.
IIRC Route 85 south of I-280 has restrictions on heavy trucks and I surmise this is why it isn't signed southbound for US 101's long distance control in the South Bay (Los Angeles) or for San Francisco going northbound.
Correct about the truck restriction. However, the controls vary depending on the vintage of the highway and I'm wondering how dependent they are/were on the truck restriction. At the north terminus (i.e. the 1960s portion of the route), controls from US-101 southbound are Cupertino/Santa Cruz. This is reinforced on pull-through signage at the CA-82 junction (that said, from CA-237 west to CA-85 south the controls are Los Gatos/Santa Cruz).
Before CA-85 was completed south of I-280, signage for I-280 south directed drivers to San Jose/Santa Cruz (now the Santa Cruz has been greened out).
From I-280 south, the control is just Gilroy. Santa Cruz is dropped from pull-throughs and not mentioned again until CA-17 south.
So here's where I wonder about the truck restriction coming into play: If you're on I-280 south and you see CA-85 south/Gilroy, that's using CA-85 as a bypass to downtown San Jose, and wouldn't that therefore imply long-distance drivers (including trucks) should use it as such?
I would use more local controls throughout the route:
Heading south from US-101: Cupertino/Los Gatos
(Santa Cruz on supplemental signage. I chose this because Los Gatos is used as a destination on the traffic time VMS but is not mentioned on any other signage).
From I-280: Los Gatos/Santa Cruz
From CA-17: Gilroy
Heading north:
From US-101: Los Gatos/Mountain View
(Cupertino, Santa Cruz on supplemental signs)
From CA-17: Cupertino/Mountain View
From I-280: Mountain View
From CA-82/CA-237: To US-101/San Francisco