1) I think your favorite names are somewhat different in style from each other, so I don't think Samuel fits with all of them, but I do think it works with some. Fits with Paige, Chloe, Rachel, Isaiah, & Dylan...doesn't really fit with Alyssa & Jaedyn. Have to say that if I met brothers named Samuel & Jaedyn, my jaw would drop. Kind of in a good way, though, I love mismatched sibsets (prefer them to matchy-matchy ones, actually).
2)
Samuel Ryder-Lee
Samuel Noah-James
Samuel John-Elias
Samuel Chance-Anthony
Samuel Robert-Quinn
Samuel Ethan-Brady
Samuel Wyatt-Ray
3) I think Samuel is a very nice name. A little common, but still very strong & definitely timeless. I think if you were to use it, you should consider it honoring yourself. I think it's so sweet when little boys are named after their mothers. However, the names sound different enough that it wouldn't be confusing or boring.
4) I don't like the nn Sam! Everyone else seems to, lol, but I don't. I like either the full Samuel or the adorable Sammy. Also, WDYT of Samson? I'm on a big Samson kick right now.