This is the actual:
#EXTINF:368,O.A.R. - Dareh Meyod
M:\O.A.R_\34th & 8th Disc 1\O.A.R - 01 - Dareh Meyod.mp3
#EXTINF:405,O.A.R. - About Mr. Brown
M:\O.A.R_\34th & 8th Disc 1\O.A.R - 02 - About Mr. Brown.mp3
My new winamp instance was some how corrupt. Still had issues with playlists. Winamp alone had no issue loading and playing but RR/Carwings/DFX did. It would load, cycle the titles, but not find the files. I made sure m3u is in the RRconfig extensions. To avoid headaches but give up a little convenience I moved my music to the local disk of the PC in question and all is well. I appreciate the help and responses. Maybe if I get a little more patience down the road I'll find what the exact issue here was.