Advice for putting together a vertical tasting

My partner and I are wine enthusiasts who happen to share a birthday. We're not experts by any means but we've been exploring the wine hobby together and just wrapped up a trip to Napa. One thing we haven't been able to try is a vertical tasting.

Our birthday is coming up in a few months and I'd like to get a few bottles of the same wine over different vintages, specifically a 1988 and 1990, the years we were born, and 1-2 more recent ones so I can host a vertical tasting for us and a couple friends.

But after searching through some vintage wine sites, I'm having a really hard time finding a wine with both of those vintages. In fact, I've not found any. Have I set myself up for an impossible task? Where should I be looking?

If it matters, I had been looking for a cab or meritage blend, but I'm not too picky about the varietal, we like a lot of different wines. I also really can only spend a max of $300 on each bottle, but even at an unlimited budget I have not yet seen what I'm looking for.