For example, If I get to 100 Two handed, will I still be able to get higher Two Handed damage bonuses with the perk that boosts skill enchanting?

In general it would also be helpful to know for all skills if you see any return for getting them past 100.

yes... skills go past 100

However... skill level has less impact on effect than the perks in the trees do...

ie; 100 1hand skill only gives you something like +24% damage or something like that.... so another +25 1hand skill will only raise damage by 6%

Of course... with 1hand the enchant is a flat damage increase... but you get what I'm saying.... Skill level really doesn't help much compared to perks or flat % boosts.

Crafting skills don't have caps. Other than maybe the memory allocated with a double.

So you max is something like 1.8 x 10^308

You start out in this game about as powerful as you need to be to finish it. It's not like an ARPG where you develope your character because you have to. You can finish any of the quest lines before you get to level 20... 10 if you try real hard. Level is more of a gauge of progress rather than a gauge of strength. People aren't used to that, so they think it's "broken". Once you understand the meaning this game has for "level" things start making more sense.

I guess what I'm really asking is do you think its worth to go up the middle of the tree in enchanting once I've already gone up the left for weapon enchants.

I want to make the best passive-bonused warrior and wanted the weapon enchanting for the extra damage. It sounds like I will indeed get a good bonus for my two handed gloves and boots from insightful enchanter to justify that extra point, if I read these responses correctly.

Thanks!