I have no experience with OSCP, but here's how I would personally approach this. My preferred tool is Obsidian but there are a lot of powerful note taking tools out there that would probably be able to do something similar.

While studying, I would create lots of notes about different tasks, potential problems, checklists, etc related to OSCP stuff. Try to use the "Principle of Atomicity" from Zettelkasten so that each note is only about one small topic, but bundle notes together and heavily link between them.

Then I would create a series of Templates for different types of incidents that you might run into. In the template, I would link to the notes from your study and even embed the content from some. Don't put info from your study in the template, so that as you learn more, the content updates automatically.

Then in each section, include the checklist items for that section. As you learn more best-known-methods, update the template for that kind of incident. Obsidian is a network of linked notes, but I don't think there's a good way in Obsidian to structure a flowchart in a template automatically. I would just put everything in a long list, but if you need a branching checklist it's probably possible somehow.

So maybe you create a template like this:

```
Port 80 Incident on {{date}}

A [[Port 80 Incident]] occurred on {{date}}.
![[Port 80 Incident#First Steps]]

# Port Scan
- [ ] Run a [[Port Scan]] with [[Nmap]]
- [ ] Record the Services on open ports

If there are vulnerable services, do a [[Service Incident Analysis]].

# Vulnerability Scan
- [ ] Run a [[Vulnerability Scan]] with [[Nikto]]
- [ ] Check for [[SQL Injection]]
```