I generally find watching in release order tends to work better than chronological order at least the first time thru. The episodes are written assuming you aware of future events depicted in previous shows, if you aren’t they tend to lose a lot of their impact.
Congrats for getting thru TAS, I have tried and I just can’t.
While I agree about starting with TNG, I’d honestly love to rewatch most TOS episodes. Every trek has had at least one main character I just could not bring myself to like, except for TOS. The show is completely different, but the character interaction is amazing. Worth noting, I also love all the TOS movies, while the first and last TNG movies I just didn’t care for.
Maybe I just need a break from TOS. I wish we got more Sulu and Uhura. They are hardly part of the show. I think Bones was difficult to watch in the movies.