What is tapirrick?
Training Peaks will do much of what you want. $9.92 USD/month if you buy an annual subscription.
Training peaks tells you what to focus on during weeks leading up to an event (muscular endurance, anerobic endurance, force, speed, etc.) but does not give specific workouts for specific days. I'm not aware of any platform which gives specific workouts for specific days. $60 or so will get a real training plan which does that or you can make up your own from the internet easily enough.
Garmin Connect will sync to training peaks so there will be no manual upload. Your workouts will appear on TP whenever you upload your device to GC.
-Tim-