I have found several issues with the challenges added by TTW:
Private Ryan
This challenge requires all 4 American soldiers in Operation Anchorage to be rescued.
It seems that this challenge is bugged as every 1 soldier rescued was counted 2 to the challenge.
Too Good to be Two
This challenge may be bugged. In my play, this challenge was achieved when the I killed the first Gary with lead pipe. It should have been achieved once every Gary was killed.
Legacy Character
The interval of this challenge appears to be 0/0.
Roasted Roach
I have killed the Roach King with a Heavy Incinerator but it didn't count to this challenge. (needs verify)
Load Order as follow:
[X] FalloutNV.esm
[X] DeadMoney.esm
[X] HonestHearts.esm
[X] OldWorldBlues.esm
[X] LonesomeRoad.esm
[X] GunRunnersArsenal.esm
[X] Fallout3.esm
[X] Anchorage.esm
[X] ThePitt.esm
[X] BrokenSteel.esm
[X] PointLookout.esm
[X] Zeta.esm
[X] TaleOfTwoWastelands.esm
[X] DragsVGUArmorBase.esm
[X] Project Nevada - Core.esm
[X] Project Nevada - Cyberware.esp
[X] Project Nevada - Rebalance.esp
[X] Project Nevada - Extra Options.esm
[X] iHUD.esm
[X] AWorldOfPainFO3.esm
[X] TTW_XPReduction.esp
[X] TTW_SuperMutantRebalance.esp
[X] TTW_StartupMenu.esp
[X] TTW_SpeechChecks.esp
[X] TTW_OutcastTrading.esp
[X] TTW_MoreCookingItems.esp
[X] Project Nevada - Cyberware Additions.esp
[X] Project Nevada - Rebalance Complete.esp
[X] Project Nevada - All DLC.esp
[X] Project Nevada - TTW.esp
[X] CASM.esp