It's not so hard to setup, but you do need a 3rd party program to do it for you otherwise it's a fucking mess. Then you make like 1alch 1chaos 2chaos 3chaos 5chaos 10chaos tabs or whatever, drop all the gear you want to sell in there, and set it to autoupdate every 30mins or whatever, and it's done.
Main issue I've found with the whole trading, and especially selling, is the constant fucking breaks from gameplay. If you sell a lot of shit, especially low cost shit, you have to basically spend like what seems to be 10-20% of your time trading, TPing back, finding the items, then back into play and shit.
That's why an AH system is so much better, in terms of quality of life. You just drop your shit on there, then later on you collect your money. On the other hand, it's a lot harder to use an AH to get really good deals like you can with the current trade system in poe, plus there's the currency shit where if you're short say a chaos generally if you ask if they want like fuses instead they'll take them, but can't do that with an AH.
Maybe if they had a system where you set up a NPC in your hidehout that sells your shit for you that'd be great, so you can just accept invite, let them find the item on the NPC and buy it, while you keep playing.
It isn't so bad self found until higher tiers of maps though. I mostly play self found, just buying a weapon or something when I need a new one, and I rarely bother to sell shit, and I do fine up to like 80-85. It's when you start going higher that you really need the good gear with right rolls and to roll your maps so you need a ton of currency so you need to sell a lot of shit.