I feel like the odd one out here. I didn't have the TG-16 back when it was still an active system, and it seems like many of you come from richer families than me, haha. I never had more than one system in each gaming generation until I bought my PlayStation in '99 (I already had the N64 since it launched), and my parents never really bought me home consoles since the average cost for them was beyond what my parents wanted to spend on a Christmas/birthday gift. The only exceptions were that they got my brother his NES in '87, and I talked my mom into getting my N64 on the agreement that I would buy my first game for it myself (but even then it was an extravagant gift at the $250 launch price). Anyway, I had to slowly save up the $100-some myself to get my SNES when I was 11. That was for the bare-bones model, since one with a game would've been more expensive yet, but it worked out because Nintendo had an offer for a free copy of Super Mario All-Stars with the purchase of a SNES (although it required me to demonstrate the patience of a saint as I had this shiny new system I was so excited about, which was also my first and only video game system in years as my brother had sold off the NES a while prior, and I had to wait several weeks for the game to arrive by mail). Back then I wasn't even aware of the existence of the TG-16. I don't recall ever seeing an ad for it on TV or elsewhere (didn't subscribe or buy any game magazines until 1995, and that was just Nintendo Power), and I don't remember ever seeing it in stores either. I also didn't know anyone who had it or ever talked about it. Although, admittedly, I didn't even know much about the Genesis, so I don't know how much was me being in a personal gaming bubble or my environment.
Anyway, 1999 was the year that I got a lot more serious (and open-minded, expanding beyond Nintendo) about gaming, and it was also when I started collecting old games, first with the goal to reacquire the NES games I loved as a little kid. Not so coincidentally, it was the year I started using the internet a ton, so I was learning a lot. I'm guessing I first learned of the TG-16 around then. At some point I became interested in owning one, but Dracula X: Rondo of Blood was the real catalyst. I had long been a Castlevania fan and really wanted to play this critically acclaimed but hard to obtain gem, and I wasn't about to resort to glitchy emulation. By sheer luck, I came across a guy on a forum selling the game for $70, which was an excellent deal back then before any US releases existed and you were lucky to get it for under $150. I sat on that copy for quite a while with no system to play it on, and oddly enough, I got another opportunity to pick up a copy which was also for about $70. I flipped that spare copy for around $150 and essentially had Rondo for free. Then in '04 or '05 my fiance surprised me with the Christmas gift of a PC Engine Duo-RX lot he got from Japan Yahoo via a friend acting as a middleman. It came with a bunch of great games and accessories, and he got a great deal himself, only paying something like $120. The rest is history from there, although I can add that it was only a couple years ago that I finally entered the US side of the system. I was participating in a Secret Santa gift exchange and the guy wanted TG-16 games, so I bought a couple small lots, gave the guy several of the games and kept for myself the system and games that he already owned. I got a few good games that way, but I'll always favor the Japanese library over what I consider a somewhat limited US library.