Hmm! I may not be the best one here to answer your questions! But I will try to shed some light on what I can.
In your first example, I would expect this to work only if the filter in Preferences --> Vireo --> Filters "Crop video filter" was turned on. Given you are doing this on the command line it's an over ride to the global settings in preferences for the duration of that session of VLC.
In your second example I think the problem appears to be Syntax:
ption An option that only applies to the playlistitem directly before it
and that overrides previous settings.
But there are no previous settings to over ride. So the command would probably be:
vlc <path>tv.m3u --crop-geometry=525x574+9+2
This also assumes that the "Crop video filter" was turned on and the setting would be an over ride of preferences for the duration of the VLC session.
In your third example I believe the last line which is source is also a Syntax error:
udp:[[<source address>]@[<bind address>][:<bind port>]]
UDP stream sent by a streaming server
However like the rest of the examples it is going to create an over ride for the settings in preferences and be in effect for the duration of the VLC session and again this assumes that the "Crop video filter" was turned on.
About the only way to get crop settings for each item in a playlist would be to create a batch file naming each of the items in the playlist and selecting the options for each of those items on the command line within the batch file. The other option would be a Auto-crop feature that actually worked!