I agree, the Caliente fork is definitely bent, not your imagination.

I don't know what year the Caliente is, but it looks like maybe late '80's. If so, it probably uses a standard sized 1" fork/stem/headset. Whether that's what the Ross has on it, I don't know, because Ross is one of two brands I've heard of, other than Schwinn, that used an oddball 21.15mm(.833") stem/steerer on some of their bikes. Nishiki is the other. Much more common on Schwinns than the other two, though. The le tour, for example, being an older Schwinn, almost certainly has the odd sized Schwinn stem/steerer, which is 21.15mm (.833") inside diameter of the steerer tube and also the quill portion of the stem that goes into the steerer tube is 21.15mm. The headsets on these bikes with the oddball 21.15mm stem/steerers are actually the same as on bikes with standard 1" stems/steerers, except for the locknut on the headset which has an inside diameter that's smaller so that it fits snugly around the 21.15mm stem.