Love that Oldsmobile in the first picture. I don't know why but for some reason, you don't see many Oldsmobiles of this vintage.
That Oldsmobile looks like one of the late '10s larger models. Maybe even the V8. A very impressive car. The radiator shell style continued to about 1923 on the smaller models, including the small four that had the three port head favored by model T speed freaks trying to get by on the cheap. I have known a few people that had Oldsmobiles of those years, but you do not see many of them.