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A couple years back at university, I created DoodleDebug[1,2], tackling some of your mentioned issues. It can be thought of as a graphical version of System.out.println(). There is a similar output format customization mechanism as toString(), but you can also customize the rendering of arbitrary types you don't control the source code of.

DoodleDebug's output is HTML-based and interactive with semantic zoom. That means you can click parts of printed objects to inspect them.

However, I didn't work on it in years due to lack of time, and even the linked description page is a bit outdated (it's not an Eclipse plugin anymore).

[1]: http://scg.unibe.ch/wiki/projects/DoodleDebug [2]: https://github.com/CedricReichenbach/DoodleDebug

Edit: Maybe this PDF of my Bachelor's thesis gives a better overview of what DD is and does: http://scg.unibe.ch/archive/projects/Reic13a.pdf




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