I work with a coach, so I don’t follow a TR plan, and I do a good chunk of my workouts outside. However, I’m a huge proponent of TR–I do almost all of my indoor workouts using TR, and I use the workout creator a LOT. There are definitely certain workouts that are better indoors, and certain workouts that are better outdoors.
Your description in the first post is basically the type of information I get from my coach and what I do when I ride outside. I will often write them down on a piece of paper and just refer to it as I progress through the ride. I could use the “workout” feature of my garmin, but I prefer not to. I just watch the time, power, and cadence, and use the lap button regularly. I think this would be helpful to people who are following a plan and want to do the ride outside. The trick, of course, is finding the right road to do these types of workouts.
I think you could make comments on the workouts about “this workout is best done indoors” or “this workout is possible to do outdoors”, to help guide users.