Well over 95% of the time, you find the same initial on both sides. But it isn't unusual at all to find special order chips with the sides different. Less usual is a design of one side and a letter on the reverse.

I have some of the two sided chips at my sales web page.
http://www.antiquegamblingchips.com/poker_monogram.htm

I'd sell for much less than $8 each:
"double-monogram inlaid chips: I have these POA series monograms that have a different letter on each side. They are quite rare. Many of those listed, I have just one chip! I'll sell them for $8.00 each:
A/F: white, red, brown .. ... .....B/D (nice chip: big C-mold): red, white, blue (blue may have a burn) .... .....B/J: red... ... . C/E: blue.... ... ... C/E: yellow (black inlays, very unusual and rare; worn); blue (worn, some small burns on inlay)... ... ... .C/E: yellow (POD-style of monograms, nice condition) ... ... .....C/J: green (sq.-edge)... ...C/P: red, blue ... ... .. C/W: white ... .... ......D/F: blue, yellow ... ...D/L: red (nicked badly, but seen on only one side).. ... ... .. F/J: red, blue . .. ... .. G/M: white... ... G/O: red, nice .. .... H/V: blue. ... ... L/M: red (or mahogany)........ L/S: yellow ... ... .....M/P: red (mahogany). ... .... . M/R: blue ... ... .... N/S: light blue.... ... ... ... .. ".

Robert