Hi, I am happy with the app I already paid the subscription and chose the Coach Jack option and it generated me a training plan, I added to Zwift the plan and I have TrainingPeaks, strava, Google Calendar synced with TranerDay but today I did my first workout in ZWIFT and there is no direct sync with this app, I thought TP synced my workout here but I just read that once a week it syncs is the day random? And if I do any freeride does it also sync? Also I would like to know if when I finish the training plan Coach Jack generates me a new plan or should I generate it myself making changes so it doesn’t generate the same training plan? Sorry for my English, I’m a little rusty. 
If you have a paid TP account we sync every week on Sunday night/monday morning or any time you make a change to your workout. Regarding plans generally it works best based on goals of 24 weeks away or something which include 3 blocks. You could keep repeating these same 3 blocks over and over again even with the same plan and continue to make gains. If your answers and strava history are similar it might make the same plan again but for sure you can change it just to give more variety. No harm in that and reasonable chance it will be beneficial.