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7) Where in all these steps is a technical or organisation or motivation problem ?
Nowhere because you studied it, then solved it.

The more changes you will have to manage, the more experience you will have, the less confidence you will have in yourself, the more you will be reliable.

6) The easy part is after: motivate, delegate, follow-up, adjust, report.
Try to be in advance.
Be fully auditable.

Delegate everything to be free for surprises. Don’t accept anything that you don’t know: you are responsible. Follow-up everything. Report the facts. Propose adjustments.

5) Then you will build the steps, the Gantt diagram, the WBS, and make your hierarchy validate the project, the resources, and the calendar.

4) At this step, you will also have to define which information or capabilities are needed by who, and how to imply/motivate who. You will have to meet the who, to listen them, and eventually, understand which cultural evolution is needed.

3) Then you can define what is the projected evolution, who will be implied, which delays will be acceptable.
Maybe at this step, you will have to redesign the evolution process.

2) Then you need to know who the processing is for. Who is involved (customers, employees, managers, subcontractors, partners), what is the processing and data flow diagram, what are the constraints (legal, security, resilience), who is responsible for what.

1) First, you need to study the system. What is it for? Is it important? Does it handle real-time data? What is the impact of the data and processing?

I have worked in a large hospital company for over 40 years, and I have experienced each of these scenarios.

This is problem dependent. Sometimes technical evolution is impossible, sometimes organizational evolution is. Sometimes a "big bang" is required, sometimes the coexistence of the two systems allows for a gradual evolution of practices, sometimes a gradual evolution of the system achieves this.

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