Hey M.O.B, I think i've found a flaw in the list.
I'm not 100% sure because I don't own the strategy guide and the Wiki isn't reliable. But i'm pretty sure the TLAD mission "Roman's Holiday" takes place after "Diamonds in the Rough" because I've just completed "Bad Standing" and immediatly after Ashley calls and says to meet her at Ray's, thus unlocking "Diamonds in the Rough".
I've already completed Playboy's missions so Mallorie is constantly calling me to trigger "Hostile Negotiation" but I just ignore it because I haven't played "Roman's Holiday" yet. Thank the gods of R* for letting us ignore Mallorie's calls
So unless i'm wrong and GTA IV is just screwing me around. These missions have to be done before "Roman's Holiday".
[GT] Blog This! [C] (Unlocks "Frosting on the Cake")
[GT] Frosting On The Cake [H] [+]
[RB] Diamonds In the Rough [=]
[RB] Taking In the Trash [-]
Now instead of rearranging the above missions to take place before "Photo Shoot", you should put them after "The Holland Play" so it doesn't stretch out Ray's missions with the Playboy/Dwayne arc. Just ignore Mallorie or put your phone on sleep to avoid "Hostile Negotiation".
GTA V comes out in less than a week so I don't blame you if you just say f*ck it.