Has there already been a thread on this?
Basically, what I am looking for is a guide for improving your skill checks with items. Perhaps something that lists items that give bonuses by skill and by bonus type for stacking purposes. Then sorted by cost. And then perhaps some situational items that do not directly improve the skill but add other uses to it (like the gloves that let you disarm at a distance, cant remember their name). I also would have to note items that help all skills like the Pale Green Prism Ioun Stone and the Luckstone and Luckstone.
I don't want to reinvent the wheel but if nothing has been done for this yet I very well may sit down and do it myself. I have a character that I'm working on that is a skill monkey and I want to improve my skill modifiers and am looking into the order I want to purchase gear in to improve my skills.
I think you probably want to narrow your focus a little. There are hundreds of such items, more if you count spells as items via wands, potions and scrolls.
Maybe aim at a group of related skills - social skills, or stealth skills, or whatever you're most interested in.