I don’t believe the operating conditions for this feature are well documented, but in my experience it has typically done the right thing. I’ve noticed in times of warmer temps it is always ready to turn on the seat ventilation (although sometimes too soon given how well the Telluride seat ventilation works). When it’s cold, the seat heat is on and ready to go before I even think about it (although it’s typically at a lower setting... sometimes it’s nice to have a quick hit of extra warm seat right away when the vehicle is warming up, so I occasionally change it on my own). Usually it has been most rare to get the steering wheel to turn on automatically, but considering that is the heated feature most aggressively turned off by the system when you turn it on yourself, that isn’t surprising.
One thing to note is that I absolutely never have my climate control in a mode other than auto (other than rare and extreme cases requiring heavy defrosting, etc). Do you operate your climate control (intentionally or accidentally) in a way that turns it off auto? If so, that may affect this feature. Honestly, I don’t know, because I don’t use mine any other way, so I can’t say I’ve tried. But that could be a possibility if you think it isn’t being as smart as you would like.
As an aside, I do appreciate that this system in the Telluride seems to have some smarts and doesn’t just turn things on at a given temp. My previous daily driver, a Jeep Grand Cherokee Summit, had a similar(ish) feature that would activate when the vehicle was turned on (only). It didn’t adjust to changes while driving. When it did activate, it was based on temperature at time of startup. If it was 40° or less, heated seat and wheel would come on. 80° or more, and the ventilated seats would engage. In general, it was fine, but sometimes the system thermometer hasn’t quite updated from the last drive. So maybe it would show 39° right at startup but quickly rise to the high 40s or above. But since it was less than 40° at startup, now my heated stuff is on, which I really don’t want at this point. Minor inconvenience, but a little annoying at times.