I honestly cannot even remember why he couldn't tell him about the obstruction.

because he is the begger the lord was looking for and was scared that he will get killed but after some time he couldnt because (my personal opinion) his brother put some kind of spell on him with the words "wait till the time is right" if he acc did that its because if the lord gets cured he becomes way to powerful for that the other lords to deal with

Aha! That's right! Thank you, friend