Is there a specific version of TS2 that is not compatible on modern systems?

As far as i know no not really. I originally had the issue starting the game because of a direct X error. But Graphics Rule maker helps every single time. There is also a way to bypass the launcher if it causes issues, or if you just want it gone (https://answers.ea.com/t5/Other-The-Sims-Games/TIP-Bypassing-the-Launcher/m-p/3351785#M8605)