Any plugins that allow this? I've searched using forums but the results aren't what I need. If I recall correctly, stuffplug used to have this feature but I believe it got removed when Live came out.

Cheers!

Nope, stuffplug 3 doesnt have this as microsoft found out and prevented this from happening, also stuffplug now is a stand-alone like MP!L and scripts cannot do this either

I doubt anybody will make it again as it no longer works, and in reality hasn't since about MSN Messenger 7.0 when Microsoft added checks of Display picture sizes at both your end AND your contacts end, therefore if you had an oversized Display pic they would only get the 96x96 middle part of the picture.