I don't see how 3.5mm plugs are a mechanical problem in pedal-to-pedal connections on a pedalboard. And most of my experience has been fairly chaotic shows with stage diving and IDGAF behavior all round. You need something stronger guitar-to-board, and maybe board-to-amp, for sure.
Definitely for guitar-to-board and board-to-amp you want to use a 1/4" jack. Personally, I like to use locking 1/4" connectors as dedicated "board in", "board out" and "amp in" jacks. Neutrik type D stuff.
Trust me: you don't want to use the thinner cable assemblies like the Mogami W2314 for long connections, which is what you would need to use for the 3.5mm plugs. I love using that cable for pedalboards because it's *very* easy to work with and tends to be quite flexible. But I wouldn't trust it at all as something that rolls around underfoot. Our cables take a lot of abuse that would make many other types of cables wince: there's a reason you don't see folks soldering up installation-grade coaxial cables to 1/4" jacks: it would technically work, but they would not survive the environment they exist in.
I'd want to hear a high gain pedal with input & output cables parallel to each other and so close together on a TRRS cable, but it would absolutely be worth the experiment.
This is possible as well. Studio rack equipment quite often uses TRS 1/4" jacks for both send *and* receive signals. It's incredibly convenient, as one can simply use a single cable to, say, add a compressor in a signal chain. You just use the normally closed switches on a switched 1/4" TRS jacks: the switched end gets a jumper between T and R. Inserting the jack breaks that connection and allows one to use T and R as send and recieve. You don't necessarily need to seperate signal grounds on these connections, a TRS will do just fine.
Studios tend to use 1/4" TRS plugs for durability and reliability reasons, because these connections get plugged and unplugged all the time. If it's a simple send/return loop you're looking to build into a pedal, it's a very convenient option.
Several years ago I decided to make all my DIY pedal jacks LTR. As a lefty, my guitar cable comes from the left, and it's reading order. But there have always been a couple Boss pedals I won't give up, and now my 16yo uses some of those old pedals and it's a shitshow. Inertia is working harder, even though LTR is objectively better, disregarding handedness.
I'm a righty, but I'm a friend of the left hand path. Hail Satan.
This is a bit of what I'm talking about though: this method of ordering pedals may make more sense to you. I can't argue with that.
But while many of the so called "romance" latin-derived languages read left-to-right, this is hardly universal across cultures. Many languages from the global East are read right-to-left: Arabic, Hebrew. Kanji and similar systems tend to be read top to bottom, and their books tend to be read from what we would think of as being the *last* page to what weould think of as being the *first* page.
So at risk of sounding like a pedant, it's not really an *objectively* better means of signal routing. I'm sympathetic to the idea as I'm American and read left to right: I get what you're saying. *Subjectively*, that makes sense to me.
The drawback is that we exist in a context outside of ourselves. All commercially available guitar gear that I'm aware of is made to adhere to a right-to-left signal path: integrating equipment that does the opposite with existing gear creates, as you have experienced, headaches.
Abstractly the idea makes more sense. In context, I'm afraid, it doesnt make any sense at all. It's an added complexity to a standardized system. This isn't always a bad thing, but there is a trade-off.
The question that one needs to make when considering such a thing is this: is it such an advantage that it is worth dealing with the headaches it creates? Is it so much better that it will cause everybody to abandon the old ways and jump on board with the new ways, therefore making the headaches short-term and insignificant? One cannot simply assume that one's ideas are so great as to overcome these obstacles.
For every Apple, you get about 10 Segways, Juiceros, and Theranos'.
Now...I'm not opposed to charting one's own path. Hell, I've adopted powercon connectors for my rack and pedalboard, even though they aren't really easy to come by in stores. I just keep a spare handy. I'm a huge fan of using 3.5mm plugs for expression cables: it just requires me to keep a few custom made cables around to integrate these devices.
And I'm not opposed to using 3.5mm plugs to connect pedals: I just question exactly how much would be gained from such a move, and how much of a headache it could create down the road.
I'm also aware of the headache of existing in a culture that simply refuses to work in the much simpler and more intuitive metric system. At work, though, I still use imperial measurements because that's what makes communication easy between myself and my peers.