By transcript, I mean every command and every response in the debug session. Usually, in the beginning, I do not know yet what I'm looking for, and set breakpoints at points that may be interesting, and when I reach the breakpoints, I look at variables. Later, when I reach the point where things have gone wrong, I can look at variable values now, but also at the result of every previous query. This helps me answer questions like: was this object here already in that queue over there when the previous request came in?
I can also attach the debug session to an issue in order for others or future me to understand what was happening then. In a purely GUI-driven debugger, I can copy&paste a stack trace of the final point, but the history is lost.
I can really recommend debugging with command-line gdb (inside a text editor, of course; we're not barbarians). The transcript that lets you look back at the past of your debug session really adds a new dimension to the debug experience that a plain IDE integration just does not offer.
Just learn a tool at a time. Ftrace, for example, is a nice tool to trace kernel events. It is not the coolest kid on the block, but simple enough for basic things.
Mermaid has explicit support for diagrams that look UML-ish (never mind the filled triangle arrowheads for inheritance): class, state and sequence diagrams. Graphviz doesn't do that easily.
Remember when Blackberry succeeded in the market by calling their text-messaging device a "two-way pager" even though, technically, it was a mobile computer with modem and not at all a pager?
Chances are you'll fare best by hiding your earth-shattering new paradigm behind a veneer of familiarity. Then nobody has to know you have deep insights no one else has.
If you're at least a bit into home-lab tinkering, you could run NextCloud from a Docker container on your NAS or home server or RPi. For external access limited to your family's devices, you could use Tailscale.
But yes, you could just have Hetzner host it for you for a handful of Euros a month.
"Is my partner having a good time": Make your partners look good. That is usually a good idea in any team.
"Find the earliest end". That would mean don't ever maintain an old product because there's nothing interesting in it...
"Yes and" principle: you accept the ideas that your fellow players introduced and build on top of them. For example, "Backend moved their data store to a novel distributed document store they read about on Twitter -- Yes, And we'll let the frontend run in a JS-emulated Browser-in-a-Browser!". I see that being applied, but I'm not sure it's good advice.
The reason why this works is that IBM CGA/EGA/VGA map their text-mode video-RAM at segment 0xB800..0xBFFF, and in graphics-mode at 0xA000..0xAFFF. MDA and Hercules, on the other hand, map the video memory at 0xB000..0xB7FF, for reasons I never fully understood.
So, if you plug a Hercules card and a VGA card, you can have two screens. Some debuggers supported it. I never got it to work back in the day with my ET4000 and an MDA scavenged from a PC-XT, but I was just a teenager with no access to StackOverflow.
While we're proposing useful words, may I humbly suggest two useful adverbs:
"fei" (Bavarian): in contrast to what I think you're assuming. "Des is fei da letzte" -- "This is the last one, and I think you thought there would be more".
"als" (Allemannic/Suabian): something like "in the default case, which is also frequent".
Bugzilla does it out of the box, even using GraphViz.
However, Bugzilla only has one flavour of dependency ("blocks"), whereas JIRA implements the whole Allen Interval Algebra (which, however, only those people use who have ever wondered why the number of Allen relations is exactly 13).
At first I thought this was a firmware mod for those calculator watches, but it's a new circuit board. Comparable in power to those TI msp430 developer watches, but with better UI possibilities.