I think that the risk of losing significant amounts of money rests with the older obsolete issues rather than the newer issues. Why? Because I believe that there are significantly more collectors of newer issues than older obsolete issues. If the market ever does "tank" .... the newer collectors in large numbers will be the first to cash out at close to what they paid for their chips (closer to face value) while the older, higher priced material will drop significantly (percentage wise)in value because of a lack of buyers/customers and the unwillingness of many to give up a once valuable item that cost the buyer a significant amount of money to purchase. There are only so many collectors who are financially able to consistently shell out hundreds or thousands of dollars for a single chip to add to their collections. When looking at the broader picture, their numbers are relatively small in my opinion.
Look at it this way. The newer collector is the standard-bearer of the collector of tomorrow. He/she is the collector who gravitates to the older classical issues as he/she matures in the hobby, much like the veteran collectors before him/her did. It has been my experience that most new collectors don't immediately focus on the older obsolete issues until much later in their personal development into the hobby. As the older chip collections pass on to new owners, the hobby constantly needs new blood to snap up the limited supply of obsolete material. With the new collectors, who may have given up and dropped out of the picture, there are fewer people to sell chips to in the future.
Furthermore, politics aside, if the economy of this country does an about face ... history has taught us that the first spending people cut back on is hobbies and leisure activities.
Just this interested observer's opinion. I'm certain that others will have a much different view of the chip world.
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