There was no realistic prospect of a peaceful settlement with Richard II, or any high lord. Those... people felt they had no obligation to keep their word when dealing with mere peasants in rebellion; 1381 was by no means the only bottom-up revolt that collapsed when the ruling elites lured the leaders into negotiations only to slaughter them under flag of truce. Almost invariably, this meant that the rebellion agreed to halt its own momentum, and in return they were betrayed, dispersed and subjugated again. In some cases, like 1381, the oppression actually worsened, at least in the short to medium term.
To win, the 1381ers would have to extirpate all or most of the military aristocracy, and fend off invasions from the continent as well as Scotland and Ireland (particularly the Anglo-Irish lords there).
The secular and ecclesiastical authorities of the time had a deeply vested interest in not allowing the peasants any kind of political success or voice, much less allowing them to topple an entire large, important kingdom.
Tl, dr: Revolt can only win if it gets lucky a lot of times, and even then it will be a long, destructive civil war to the knife, followed by a long, destructive period of "regular" war, also to the knife.