1-2. a little over a year
3. 1,5 seasons
6. Usually I have everything needed to repair the boat by the time I complete the community centre so right after I complete it.
8-9. Year 2+
10. The second or third day after going to ginger island
14-15. Y 3+
25. I only did it once and it was Y 7 (first play through) and then I got close to it on another save in early Y3 but then I accidentally deleted the save.
That's how long it takes me in vanilla. Recently started playing modded stardew and now i don't rush stuff, prioritizing exploring new things added by the mods, so my progression's slowed down a bit in some aspects.
Also I skipped a lot of points on your list just because I don't remember by what time I complete them