Would it be possible to generate .ics file of our planned workouts in TD and sync it with Apple calendar?
For ICS file we have it now on my plans. But this is static so it’s one time process. Is that what you want?
Download from calendar or dynamic URL based seems like it would be even better.
The static is not clear for me 
If I will make any change in the TD calendar, will it update in apple calendar or not? If not, for sure I would love live version 
Yes, changes in TD calendar will not automatically update. I think this is a good idea so we will try to add this, but it will take a bit of time before we can get to it.