In its beginnings in the Dark Ages, medieval feudalism was pretty risky for everyone involved (though less risky than a complete societal collapse, but that is a low threshold for judgment). The nobility was expected to defend the land against invaders, who came in droves (Vikings, Magyars, Avars, Pechenegs etc.), and the incessant warfare came with a high risk of death. The peasants were mostly unarmed and any enemy attack would cause them great harm. Not even the clergy was sure to survive such events, as most of the invaders were pagan and would gladly kill priests.
We tend to judge the whole feudalism by its late stage, when pampered barons lived in huge estates and their only real risk was eating and drinking themselves to death, but that was also the stage which led to the system's demise.
That's not even the main risk reduced. Feudalism was invented to reduce risk of dying of starvation. Peasants were always 1 bad harvest away from starvation, they couldn't store wealth for more than a few years (as grain which goes bad). And their labor was either almost worthless (most of the year) or in shortage (during the harvest and a few other occasions).
So they did "cloud farming" :) The people who had access to wider markets and had enough wealth to be able to survive one bad season - provided the infrastructure and shouldered most of the risks. In exchange for the only thing available to peasants - their labor.
As any power hierarchy it quickly turned to shit, but the idea was sound.
Hmm fascinating! So the real "best of both worlds" here is to try and stall the march of entropy where the services we rely on "tun to shit" as you say.
One way i've been thinking of this is crowd sourced alternatives to major apps but the problem with this is the backends. Lets say you make a anti-enshittified youtube client. Well youtube is just gonna change their backend to break the app. Well now you gotta have crowdsourced efforts to constantly reverse engineer their backend.
We tend to judge the whole feudalism by its late stage, when pampered barons lived in huge estates and their only real risk was eating and drinking themselves to death, but that was also the stage which led to the system's demise.