Wow, great trip report, noel! Found myself smiling and nodding through the whole thing.
What can I say about Elmira? It's got Mark Twain's childhood home, I guess.
Uh huh! Definitely not a world class city, so that suffices!

NY 14 wasn't a terrible drive, except near Geneva. Do wish the Seneca Lake views were more frequent.
Yes, Geneva is a slog. You can use part of US 20/NY 5 (Lake Front Drive) to bypass the downtown area, but a proper alternate for north/south traffic is badly needed. Ditto for Watkins Glen, of course.
I took exit 18 there onto NY 31 west to Dogtown! A venerable Rochester institution, where I enjoyed their version of the garbage plate - two hot dogs on top of a bed of mac salad and home fries. Paired with a bottle of Stewart's, I felt like I was truly an Upstate New Yorker.
FTFY! But yes, definitely!

NY 104 was a pain in the rear to get through; 2 lanes east of Webster, for the 50 miles to Oswego? With traffic lights? Ugh. I stayed on NY 104 for 25 of those miles, exiting onto NY 14
It's a nice highway through Webster... if only the freeway extended a bit further. The two-lane portion is known for parades of 20+ cars forming, as traffic allows almost no passing opportunities. Williamson to Sodus is the worst. Glad you got to experience it though, as it's one of few real Super 2's in Upstate New York. I suppose one can always dream of a second carriageway...
Sounds like a classic Chimney Bluffs experience too: sorry about the sun, we've had plenty of that lately!
We took I-81 all the way south home from Syracuse, arriving home at 3 AM on July 8th and exploring more of the state that most New Yorkers probably have in their entire lives.
Likely true, because of New York City. I know I'm an exception, and I like to think that everyone else north of the 42nd parallel has done their share of exploring, but that still leaves millions of people from the city that probably haven't seen much of their own state.