Fantastic question! First off, as we talked about at the bike handling clinic, you really should not be using your aero bars in group rides, crowded trails, etc. You have significantly less control in the aero position so it’s purely a safety issue. In fact, many group rides (roadies) won’t even allow you to ride if you are in a tri bike.
Bottomline, use your conditions to dictate the bike that you ride. If you are riding Skyline, for example, you will be much happier on your ride bike. The only caveat here is getting closer to race day. You really want to do your race specific workouts on the bike you will be racing on. It’s also helpful to train your neck muscles throughout the season so you should be doing some of your workouts in the aero position. Otherwise, allow your environment to help you make the best decision for you and those around you.