So...I have restarted at least 8 times on my game. Finally, I've settled on a race and getting the hang of playing.

My problem is with enchanting...

I'm trying to craft better alchemy gear, so my enchanting potions will be stronger.

I have 4 pieces of apparel: 2 are at 25%, but two are only at 22%. Is this why i only get 27% fortifying on the potions?

Also, I made another one and it said the potion was at 29%...So i tried to upgrade my alchemy armor again and it never changed.

Obviously I'm not doing something right...

Any help would be great!

Once you've enchanted an item it cannot be enchanted again. You'll have to find (or craft) new, unenchanted armor pieces and apply the enchantment to them to see an improvement in the effect.

What Gator said you have to keep crafting gear to or buy some cheap clothes at Solitude and enchant them. My advice is just don't make your stuff so op the game becomes really boring. I did that once and really regretted it.