I've given this a go and this appears to be the easiest method for adding Scottie Pippen as a coach in NBA Live 08.
- Copy Scottie Pippen's face (scpippe.fsh) and headshape (scpippeB.ebo) and rename the face file scpipp_.fish and the headshape scpipp_C_head.ebo. Make sure both of those files remain in the sgsm folder.
- Using DB Commander, open coaches.dbf and locate the entry for the Bulls; depending on whether you're using a roster update, that will either be Scott Skiles or Jim Boylan.
- Change NAME to Pippen and FNAME to Scottie.
- Change the COACHID to 8043 (90's Coach; this will prevent the game from using Skiles' audio, though obviously it still won't be accurate).
- Change HEIGHT to 79 and WEIGHT to 228.
- Change COLOR to 3 (if unsuitable, try 4) and leave BODYTYPE at 1, EYECOLOR at 1, EYEWEAR at 0 and SUIT at 0. Also leave the TEAM assignment at 3.
- Change ID7 to 90COACH and PLAYERPKG to SCPIPP_. Leave BEHAVIOUR at 0.
- Re-load the rosters/saved file. Scottie Pippen should now appear on the sidelines as the Bulls' coach and wherever a coach's name shows up in the game text, it will read Scottie Pippen.
Note that you should be able to do this with any player, you'll just need to extract their face and headshape files from the .vivs unless they already have those files "loose" in the sgsm folder (such is the case for missing Legends like Jordan and Pippen who have been added through unofficial patches). Just make sure you assign them a different PLAYERPKG (eg SCPIPP_ instead of the usual SCPIPPE) and rename the files accordingly. Also make sure you rename the headshape file properly (_______C_head.evo where _______ is the PLAYERPKG).
Using this method will allow the game to recognise one face file for the player in the rosters as well as allowing you to assign their face as a coach.