The video game market is a fickle bitch. About 10 years ago I bought a Cheetahmen 2 for the NES for $100. It was a rare, sealed game, but it's notorious for being bugged because the developer never fully tested it before releasing the game. You can't actually finish the game. My buddy, who was also a collector at the time, thought I was stupid for paying that price. Now Cheetahmen 2 (The original, not reproductions) will go for at least 4 times that price, and sometimes in the thousands. I've also got a Caltron 6 in 1 game that my buddy picked up for me at a flea market for $5, that one goes for thousands on Ebay.
On the other hand, there are other games that were once worth serious cash and have since dwindled to nothing. Games like Chrono Trigger and Marvel vs. Capcom II used to fetch pretty good money at the turn of the millennium, and then years later they were re-released and it killed the market. Chrono Trigger on SNES has somewhat gone back up in value, but it's taken some time.
As far as Virtual Boy, who knows if it's value will go up or down. On the plus side, so many of them have turned to garbage over the years, if you have a working one you stand a chance at the value going up if it remains in working condition. On the downside, it was so unpopular you're unlikely to see a lot of people looking for one for their collections unless they absolutely must have it. You typically see values shoot up when collectors start creating a high demand for an item that's in short supply, like a Nintendo World Championship NES cart. On the other hand, you don't see too many game systems on their own that have shot up in value. Typically only rare 2nd editions, like the NES top loader, have garnered value over time.
I'm with you. Pokemon was before my time, as was Power Rangers. I remember being in high school and Pokemon was getting popular. I kept thinking "Glad I didn't grow up in this era."
