I got a VirtualBoy used some months ago, continuing to fill out my collection. I must say I found its popular negative reputation to be a gross overstatement. Yes, you ought to make sure it's not egregiously misadjusted, but it's not difficult to play... for that reason. The primary, and largely unavoidable difficulty with VB is that there's no good way to play it. You need a large, clear space on a table which is just the right height for the VB to be at eye-level when you're in whatever chair you're using, and yet it's a "portable" system, so it's hard to feel it's worth making an installation out of.
I can tell that the system has some decent horsepower for its day, and a few games are quite good. Warioland is a must-have, Red Alarm and Vertical Force aren't bad picks, and even the generic Mario Tennis and Galactic Pinball work surprisingly well. But with a library of 22 games- 14 to the US and 19 to Japan with some obvious overlap- there are a truly crippling number of stinkers, and more damningly, stinkers made with high-profile IP. Mario Clash and 3D Tetris take the gameplay you would expect from the title and do it wrong, Panic Bomber sounds great up to the title screen, after which you realize it's not at all Bomberman and not a particularly good falling-pieces puzzle either. Waterworld is apparently rare and expensive... but I have rarely played a more lackluster movie IP game. Bowling, Boxing, Baseball and Golf round out the sports offerings, but I must say none have sounded interesting enough to compel me to put the cartridge in the system and actually try them. Haven't spotted Jack Bros. yet or I'd likely have tried it.
Now, speaking from experience, I can say it is legitimately tricky to find a game mechanic that makes such good use of 3D that it wouldn't work in 2D, and if VB had been allowed more time on the market, there may have been some better games, but a library that's on the order of 30% deadweight with only a couple gems isn't going to sustain any system very long.