Mike, as you may suspect, there are no real definitive answers to the value question...that comes from years of experience, using the price guides available, talking amongst collector/dealers that are deeply immersed in the genre of chips/items that you are interested in. Keep asking questions and get to know as many chippers as you can, try to make it to the annual show in LV, try to attend any local shows that you can reach...ie Casinorama, Great Lakes Show. Join any local chapter of the CC-GTCC such as Atlantic City; Meetings every other month, Houston Chippers every month, Florida Chapter 4x a year. There also are other groups in, Chicago, Kansas City, Biloxi Area, New Mexico, Seattle and the Ohio Valley...and I probably missed a few.
Check the Chip Board regularly, lotsa info here. Check Ebay, just for info...lotsa info there but you need to be very wary.
Do not be afraid of approaching any one that posts on this board for info...most will be happy to talk/emai you with some answers...
Welcome aboard...
Reggie