I’d recommend release order because there are callbacks and crossovers, cameos, etc. that tie these shows together. You could watch the in any order, but you’d get more enjoyment out of picking up all the references and easter eggs. So, TOS -> (maybe TAS) -> movies 1 through 6 -> TNG -> movie 7 -> DS9 -> VOY -> movies 8 through 10 -> ENT. Then modern stuff like DSC, SNW, PIC, Prodigy, and LD.
That said, there’s no need to watch every single episode of every show. Back on Reddit there were guides of “essential” episodes for each season of every series. Here’s one for TNG. I’m sure you could find this for other shows too.
Most of the time I use assistant to either perform home automation tasks, or look stuff up online. The first one already works fine, and for the second one I won’t trust a glorified autocomplete.