Pimp My Pirate~

I don't want to go bankrupt though.. O.O
I just want to make the most IMPORTANT upgrades on my equips.. that will allow me to deal the most damage and/or train the best.

We did do this, you are just too stubborn. Get Maker.

Why would I 100% DEX my Red Viska if I only need DEX in the first place so my Level = my DEX.. and I am already past that.. why can't I scroll for STR?

Strength scrolls aren't exactly cheap. Being over-dex'd is not the end of the world, just level up more and the gap will close soon enough.

Also, how am I going to replace my shoes and earrings.. or are they okay?

Forge some shoes via Maker and throw in a strength or dex crystal, whichever you prefer. Earring are not a wise choice with your funding.