I am a fan of structurizer and the C4 model in general.
I would use a single .dsl file and add the relationships and entities as you discover them. You can apply tags , and then write filtered views to only show specific tags for sub systems or workflows that a user will follow.
you can pair this with markdown/text notes that reference the png files of the views that structurizer will output.
To expand with my personal experience, I self host a synapse server partly for the reason that i want my children (aged 8-14 now) to have a communication platform they can access to get ahold of me with out requireing a sim card. I do not federate, and i do not allow account sign ups. That keeps a pretty isolated instance while still allowing everyone on that homeserver to be able to talk to each other.
I help them get Element setup on each device. I dont think this is overly complicated, but i am sure i am a horrible judge of complexity… They have to enter the url of the server, then their password, then they need to scan a qr code/verify from an existing device. Or, they need to enter a second passcode to verify their identity. I help them keep those secrets in bitwarden, so imo, that complexity is an opportunity to explain some opsec and encryption!
For keeping track of tasks on my projects i use todo txt. For each of my projects will drop a file named todo.txt in the root. each line is a task, and i order them based on priority. I can walk away from it and when i start working on the project again, i have an simple way to see the list of tasks i have laid out for this project.
I personally find it less useful to see the “big picture” of all tasks, and this lets me focus on the details of my projects without forcing a bunch of structure.
VS Code’s extension system makes it pretty easy to build your own code snippet extension. I use my own private extension to easily “generate” different types of markdown files (ie readme vs a troubleshooting guide) from my personalized snippets.
I agree that data staleness is a limiting factor. Depending on your needs and technical proficiency you could use use their zimit service (limited in the number of links it follows). The zimit tool is oss and on github, so you can run the it yourself to keep the sites you are interested in up to date in your local kiwix
While not a solution right now, I just want to add that the general transit feed spec aims to solve the data interoperability of different transit systems. The transit system keeps a publicly accessible zip file up to date, and then anyone can pull/parse the schedule/prediction data in a consistent way across transit systems. I know in the us adoption is slow, with vendors prefering to build their own walled gardens and transit agencies lacking the vocabulary or skills to advocate for more open data/tools
It looks like there is one here:
https://kevroletin.github.io/feed.xml