I have been working on a EditorWindow inside Unity to display logs from iOS device.

I have faced multitude of problems doing this, from the weird legacy UI, the not documented event system, to resetting of state of EditorWindow between play mode enter/exit (the whole class gets reset, static constructor gets called each time you exit play mode, static members are nulled).

Most of the tooling I would be creating does not necessary need to be inside Unity but I thought that by using one unified place to create tooling long-term support will be easier. Unity will really be the IDE I want it to be.

The problem is that after more than 32 pomodors I am still not close to finishing the logging editor. I want to create quite complex AI tool after that and I am dreading even attempting to create it with the legacy UI and Unity.

Have you created something more complex inside Unity editor? Have you used any helper libraries (to deal with UI immediate mode)? What resources have used to learn? Best practices?!

What advices would you give me? Should I persist (in the idea that it will payoff in the future) or should I do my tooling in something more comfortable (and with much, much more info and support) like html5?