My guild is rather small - our 240 character roster is mostly around 25-30 actual players. We raid somewhat seriously, but not in the racing mind of getting any kill achievements for the server.
We have 2 raid teams. Main and Alt. I lead both of them with the other officers being delegated on Tank - Heal - DPS advising. I put out tactic simplifications, look at the raid composition and such and... work as the Master Looter.
We don't use DKP or EPGP... =/ We simply don't have the manpower to even have rotating people in the raids. (Heck, on first day on 4.3 we went 9manning and no bloodlust in group >_> )
Our loot rules are simple: Main spec over Off spec -> Main character over Alt character (we keep tabs on who is an alt)
Of course to add into that I do look at the EJ and such for every spec to know what exactly even benefits more. Then we /roll, highest roll wins unless the player decides that it's better to give a greater upgrade to the others than himself.
My problem is myself. I rampage online, invite people, set up the MT and assistants, check enchant scroll to Guild Bank, possible gems and make sure our cauldron master has at least 3 cauldrons... with all that hassle I forget easily to put on the Master Looter. =(
TL;DR - Is there an Addon that reminds you to put on a certain looting system or something?