Good point. Still Benny's smart he'll find away. Also if you did not do it another person would have taken that job. Another person would be asked to go in. If not a robot would take it into the Lucky 38. At some point the chip will have to get inside which means the door has to open at some point.
True, but there are only two real ways that could happen.
Benny puts the chip somewhere a securitron will find it, then stealthboys in behind them and hopes that he doesn't get spotted before he can find out how to shut off house.
Benny gets killed and the chip is taken in by either a new hired goon, or someone that works for Cesar or the NCR follows in after them and has the same problem Benny had.
...
No, wait, I think I just figured it out.
Benny gets Yesman to pose as a normal securitron, then follows him inside of the building when he goes to take the chip to house. I bet that Yesman would be able to figure out where House was within moments.