I've had a 2 band 1989 Stingray since the early 90s and it has been my main bass and reference for playability and tone since then. For years it was my only bass so always feels like 'home'.
I recently picked up a Stingray Special as wanted to try the new 3 band EQ and to not rely too heavily on the 89 as a primary gigging bass. I'm really loving it, but the tone is quite different, especially the treble quality which to me seems 'sweeter' but not as transparent. The midrange character is also subtly different to my ears. It can get very close to the tones I like from my 2 band when bass and treble are cut. Boosted it sounds great, but different. In a band setting it's not huge, but I am already appreciating the bigger range of tones on offer. In summary I'm really glad to have both as they offer similar ground in the things I like about Stingrays, but different enough to justify having both!
There's really great choice if you're in the market for a Stingray now, either pre-2018 used, the Sterling ranges etc etc that you're bound to find something you're happy with at a price you're comfortable with. I managed to pick up a new Special for not much more than I see then go for used, so deals are out there if you are flexible about colour and fingerboard material.