Content creators: "Simplest" vs. "Flexible" gameplan?

Hi Warriors!

In creating an information product in the "how-to" area, one comes across a "spectrum" of possible layouts of the product. It might look something like this:

Simplest <----------------------------------------------> Most Flexible

By "simplest" I mean it's virtually foolproof. There's only one "path": first, you do Step 1, then Step 2, and so on. The information is presented in a sequential manner, and everyone goes through the same steps. In terms of packaging the product, regardless of media, you might be looking at one big item, or, at the most, different "levels" of the same item. (Example: How to Get In Shape, Level 1, then How to Get In Shape, Level 2, and so on).

By "most flexible," I mean that the creator of the product is responding to the fact that different people will have different needs, come from different backgrounds, work at different paces, and so on. The ideal product in this vein might consist of a family of smaller books/videos/whatever, each on a different sub-topic, or perhaps some that contain extra info/exercises for those who need them. For example, continuing with the niche of "exercising," (I know, that'd be a huge niche), then the "most flexible" version might be "Warm-ups," "Upper-Body," "Lower Body," and even things like "Diet," or "Extra info about Warm-ups, for People Who Need to Know More." There are two points to this example: first, the product COULD contain the same info either way, but there could be consequences to the way it is perceived by the market, depending on which way you go. Second, they may NOT contain the same information. The "most flexible" version MAY contain extra info, info that would not be needed by some, but which would be very helpful to others.

My question to you: how do/did you navigate this issue in your own product(s), and WHY?

Here are the pros and cons as I see them:

Simplest:
Pros- easiest to understand what the product is about, for the prospective customer; easiest to follow, for the paid customer.
Cons- it forces everyone to work at the same pace. Also, a single (or a small number) of products might lower the perceived (monetary) value of the "system" overall.

Most Flexible:
Pros- Allows more people to work at their own pace, giving a sense of a "better individual fit" for an individual customer. Several products offered together in a package might raise the perceived (monetary) value of the "system" overall.
Cons- Could be harder to understand the concept of the product for the prospective customer. Could be hard to follow, for the paid customer.

I will add one more thought, which, if the above didn't make any sense, will hopefully shed some light on where I'm going with this: I work in a "how-to" niche that involves people from VERY different backgrounds. As such, I work individually with people effectively, but quite differently. For example, Person A might need 2 months of slow-paced instruction with lots of extra explanations and exercises in order to understand and apply certain concepts, while Person B might get through the same concepts in only 2 weeks, needing much less explanation and working at a much faster pace. I can teach Person A, and I can teach Person B, but what to do for "Everyman/Everywoman"?

Thanks!