My take:
1. How long was the death of the mom to when he started dating?
I don't know.
2. The kid came home from school for lunch one day, ... Wouldn't his friend also need to be in school? Can they just mosey on back to school whenever?
It never occurred to me that this would be confusing. At the time, it was absolutely typical for Mom to be a housewife who was almost always at home (still pretty commonly 1 car per family, that was at work with Dad). In areas with enough population density for elementary school kids to walk to school, it was also common to go home for lunch (and come back 45 minute or an hour later; not "mosey on back to school whenever"; the afternoon start time was just as specific as in the morning). The elementary school that I went to didn't even have a cafeteria, the few kids who needed to eat lunch at school on a given day would all go to one classroom to eat their bagged lunch. (Nobody came to my elementary by bus; even in high school only a tiny number from the furthest corner of the district had a bus.)
3. What did Dollye Daly's (Stella Stevens) drum solo have to do with the courtship of eddie's father?
It had a lot to due with the courtship of Jerry Van Dyke's character. That whole relationship acts as a counterpoint to Tom Corbin's main relationship through most of the movie. One is looking for a long term mate (at least partially for the role of step-mother) and latches onto someone who only really fits with him for dating. The other is looking just for "a few laughs" dating and finds themself with someone who meshes perfectly as a long term mate.
4. Did Elizabeth Martin have to take Eddies temp rectally just to establish she was indeed a trained hospital volunteer?
Nope. That was just pretty standard for taking the temperature of a small child back then. Home thermometers were still just an awfully breakable glass tube with mercury (pretty toxic) inside. At least until you were old / mature / calm enough that adults were *certain* that you wouldn't nervously bite / clench your teeth on the thermometer (even while stressed by being sick), you got your temp taken rectally; parents at home as well as the medical professionals. And, yes, in my experience households tended to have separate oral and rectal thermometers.
5. How did Mrs. Livingston's spanish lessons contribute to the story?
They serve to keep the fact that Mrs. Livingston is moving to another country, and is therefore only a temporary childcare solution, in the audience's mind. The clock is ticking on Tom being able to rely on her to take care of Eddie after school or during school vacations. This may contribute to why Tom proposes to the first woman that seems superficially suitable. (When almost all Moms were expected stay home with the kids, reliable day care [as opposed to baby sitters] was much harder to find. I don't remember ever even hearing the phrase "day care" when I was a little kid in the 1960s.)
6. How did Dollye Daly's bowling lessons for Norman Jones contribute to Eddie's courtship?
See the answer to question 3), above.
7. Do they still have men in arcades that will paint your picture (head) on a tie in New York?
I have no idea. I have visited New York only once, decades ago when I was about 10.
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