Fred, Your post got a lot of clicks, but no responses... probably because it's a pretty broad topic to tackle.
Having said that, here's a few observations --

As to Deadwood and Colorado chips obsolete chips -- the market for such chips is pretty cool right now, except for the "key" chips in each area, like the Capone's $5 in Deadwood, the Aspen chips in Colorado, etc. For most, value is face plus a little for Uncirculated, and face-only or below-face, if it's used condition. This is a generalization though, and for better pricing research, I recommend you use ebay "Completed Items" search capabilities. A quick search revealed about 400 completed Deadwood auctions, though a number of those were unsold. Spend some time on each key word / area that you're interested in.

As to Las Vegas obsolete chips, under $30 TCR list prices, in the aggregate, those chips typically go for face or face-plus-a-bit, to an upper limit of low TCR less 10-20%. But there are many exceptions, even at these levels. The LE chips at this level may not sell, even at face value, while older chips, in mint condition, may do better, even if they are relatively common. It's just tough to generalize too much. Again, I would recommend doing some ebay research on "completed items" for the specific chips or types of chips you're interested in.

Sales on the BB will cost less in transaction costs. You won't have to pay ebay listing & commissions ... but you'll have a wider viewing on ebay, so IMO, its pretty close. You'll have paypal fees either way, if that's how you plan to settle transactions. The other thing about ebay is that you can start a chip low, and get competitive bidding, if it's an "in demand" chip. Whereas you need to be comfortable with your asking price on this BB, since it's not an auction format. For better results, I do suggest you offer a bunch of chips in the same listing cycle, whether ebay or BB, with a flat shipping fee, regardless of quantity. That allows the buyer to spread shipping cost over several chips. Otherwise, at this level, shipping costs can get pretty expensive, as a percentage of the chip's price.

These are just some broad, general observations. For any individual chip situation, the true answer is "It depends."