I wouldn't even count a pin on this list unless it tops it goes for over $500. Which would cut out these mentioned previously. A couple of those are under $100.
Main St. Electrical Parade spinner LE 3500
POTC Jail Scene (either silver or gold) on card
Flubber Mystery Pin
Wet Paint (Donald)
Born to Shop
CM Stitch C ticket
Haunted Mansion Holiday 1st event stained glass LE 150
Haunted Mansion "Gate" pin
Anyways, in no perticular order I would say.
65 Year Service Pin
50 Year Service Pin
45 Year Service Pin (I have seen these three pins in person and used to have one of them, Im sure there is a 55 and 60 year service pin but I have never seen one, either in person or a picture)
LE 10 2007 September Pin Event Figment Completer Pin
Figment in a Tux
Adventuerers Club Graves Costume Pin (probally dosen't belong on this list, but I had to give up way too much to get mine)
LE 25 Figment Framed Set (yeah, I know, its 4 pins but it was one set)
LE 50 Happy Haunts Gift Mini Pins (yeah, more than one pin but the set is often in the $1000 range)
1980's Scared Mickey Haunted Mansion Pin
Club 33 Member Walt Disney Locket Gift Pin
Not a Top 10, but I can't think of anything else off the top of my head in that super high level.