About your last request: I've previously used https://www.charlesproxy.com/ for analyzing all traffic from my iPhone and it works quite well (you use your computer as a proxy for the phone). There's a guide how to in the FAQ https://www.charlesproxy.com/documentation/faqs/

I prefer Mitmproxy https://mitmproxy.org more than Charles, and it is opensource.

To each their own, but I can't imagine a CLI being more convenient than the charles / fiddler GUIs for the kind of things I did with them.

Give it a try. I was in the same boat but found it's cli interface very well done and easy to use, especially the curses based one.

mitmproxy recently introduced a web UI as well. It's still very early, but definitely something to try out!

If you have feedback regarding the web ui: We are very receptive to that. :)

I've used Charles for quite some years now but have never been satisfied with how heavy it is (it's much better now then it used to be, but still) and how hard it can be to configure some times, even after all these years of using it.

Are there alternatives (with a GUI) for this? Been thinking about building my own....but I'm already "working" on a hunderd other projects..

Proxie (formerly known as Cellist) is nice and lightweight, and Mac native (not Java based like Charles)

Not affiliated, just a happy user.

Potatso 2 (not lite version) has a simple network log feature but for now it only contains the hostname. Request and response details will be added in a few months.

Does this support keys and custom ports for SOCKS over SSH?

Do you mean SSL/TLS?

Not yet. Sorry for that.

If you jailbreak it that seems likely to exist