The only time that is important during the entry is, per your example, the 1 min. outbound on the teardrop entry. Once you hit that 1 min., start your turn to intercept the inbound course. Its not required that you time from your course intercept to the VOR on your intercept, but you can do it if you want. I didn't usually have my students do it because it didn't offer much in the way of information for how to adjust your outbound leg to make your inbound 1 min. Then start your time when you are abeam the VOR (or wings level...doesn't really matter) on the outbound leg. Usually, baring any extreme winds aloft, my first outbound would be 1 min so that I could get a baseline time for the inbound. The ONLY leg that has to be 1 min is the INBOUND. Then I would adjust my outbound leg on the next legs to make my inbound 1 min. For the wind correction, once you get established inbound to the VOR on the entry, look at the wind correction. You will then triple it (someone correct me if I'm wrong, its been a while) and thats your outbound heading.

Hope that makes sense. Good luck!