Miami with Sunny Isles (and some Miami Beach on the right) in the background. If this was taken on a clear sunny day you would be able to see Fort Lauderdale but in this pick its sort of washed out in the center/top of the pic: https://www.flickr.com/photos/randrewlove/52270890765
How about 4 skylines in this one shot (starting west of the financial district)? …well sort of 4 if you include the mini-skyline cluster of the 1. The Well in the foreground + 2. Garrison Point (right of centre) + 3. Humber Bay (further right and behind)… and 4. a glimpse of Mississauga even farther behind of the right along the horizon.
Is it possible to get the San Jose skyline in the same shot as Oakland and/or SF? Or is it just too short and too far south?
Probably too far south. There might be a way you could get all 3 if you were able to get a shot from some mountain peak or other high point in South San Jose, getting SJ in the foreground, and then SF and Oakland to the left and right of it. But I haven't seen a shot like that at least in recent memory. SJ is about 40-42 miles from SF and Oakland both from a straight line. It'd have to be a really clear day after a rainstorm or something.
San Jose hardly has a skyline, let alone one that could be viewed from any distance.
Yeah. To even have a chance, SJ would have to be in the foreground of such a shot. Even then, it might be too far to see SF. I think the furthest south I've seen the SF skyline is from Mission Peak in Fremont.
You can see the SF and SJ skylines at the same time, though it's a lot easier from the SJ side, because the SF skyline is a lot taller than the SJ skyline. Here you can just barely see downtown SF poking out above downtown SJ: