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The other day I was in one of the local gun shops, and the owner happened to be in there. A fella came in and asked about getting a problem fixed on his rifle he had brought in, (sorry, I don't remember what the problem was) but anyway, the owner said that it was out of his expertise. He told the customer he was sorry he couldn't help him, and that he had a ad running nationally for a Gunsmith, but wasn't having much luck. Man...for an unemployed guy (me), I wish I could go back 15 or 20 years and start over. How long has there been this shortage? or is he just having bad luck?

In my experience, there is not a shortage of gunsmiths, but a shortage of people willing to pay for a gunsmith's services.
I put myself through college as a gunsmith in a suburb of Detroit.
You can feed yourself, but that's about it.
Hourly wage. No benefits (Sick-time, medical, dental, etc). No retirement plan.
Two of the other guys at the shop were retired military collecting pensions.
Another guy was married to a manager at GM.
The Boss's wife was a CPA.
It seemed to me that the only way to do gunsmithing for a living was to not need the money.
I can't tell you how many times we quoted a job only to have the customer say it wasn't worth it and leave.
Add to that the fact that K-Mart and Wall-Mart were selling guns retail at a lower price than we could buy them wholesale and you can see how it was tough to turn a profit.

I know there are a few guys who make a very nice living at it, (Wilson, Clark, Obermeyer) but they are the exception, not the rule.

This is my experience, YMMV.

When I retire from my real job, I plan on becoming a gun smith/piano tuner.

I figured out quite some time ago that If I want major work done, it's going to involve shipping my gun. If it's something simple, I can buy the tools/parts required and do it myself, faster and cheaper than any local smith can.

The real shortage is in GOOD gunsmiths.

Years ago I sent a Ruger Redhawk out to a nationally-known revolversmith, the subject of more than one feature story in American Handgunner magazine.

What I got back was a non-functional lump of iron I had to send back to Ruger to make functional. (Ruger's people told me there wasn't a square edge or sharp corner left on the internals anywhere.)

So . . . BE CAREFUL who you have work on your guns.