I sell mostly all Chips, Dice, Tokens and Currency right now. $1 and $2 items, some as high as $10 or so.
Haven't paid a listing fee in ages, I only post the 50 (now 100) items a month and then a blitz of everything when they have one of the free listing periods. The 3x free repost helps too. I don't have a store, as eBay's calculator says it'd cost me more...

I do eBay as a "fun" hobby to keep me occupied, and make a few bucks to buy new toys.

Depending on what the level of collectability of the Gentleman's $5 chips, he may be more in my Five and Dime league than your higher dollar sales.
Note the recent sale of the 600(?) $5 chips collection that went for about $3 per chip. When whoever goes to turn those, and sells them, bet that a large number won't sell for over face value, if that, in this current market on eBay.

Link to my eBay sales:

http://www.ebay.com/sch/sgobel/m.html?_nkw=&_armrs=1&_from=&_ipg=200&_trksid=p3692