I was recently posting and searching on another forum and noticed how much easier it is to shop around on there since the classifieds (okay, that's pretty much the whole site) are subdivided a lot more than they are on here. Maybe "Tack and Equipment" classified could be divided up into sub-forums like: English saddles, Western saddles, barn equipment, rider apparel, etc. Also, there could be a sub-forum for "all the time" type classifieds - like ads for people that make browbands, bareback pads or offer training services.
I posted some stuff for sale a couple of days ago and there were so many postings in our classifieds that it was on the second page (aka less noticable) within a few hours. Dividing it up would help this a lot (and decrease the need to "bump" postings so often).