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ok a few problems with your assumptions.
1) sneak attacks are d6's not d8's, im assuming this is simply a typo.
2) TWF and the improved versions require a full action to deal the additional attacks, ANY movement greater than a 5 ft. step breaks this
3)Flanking requires tactical placement, and thus you would need to MOVE to do it
4) poisons are very weak and easy to overcome so they are a non threat
5) at 5th level you are going to be lucky to get a +1 weapon/armor, let alone any of the nice things like belts or tomes, these are a progression which means that even when you get the better things the amount of damage your dealing means less and less.
TL;DR your assumptions don't take into account how often you are likely to get everything just right to make this build work, and if you are dming and NOT moving your monsters around the board knowing full well that your rogue needs to stay put to get all his hits off, then you are doing it incorrectly. you have to utilize the same tactics your players use in an encounter, it is after all a tactical war game with RPG elements :)