Don't you agree that House made some really strange decissions?
He spent over 800.000 caps to find the disk and when he does, what does he do? Hires a courier! Even if Benny wouldn't have (almost) killed the courier, it's a very dangerous place; Fiends, deathclaws, Legion, traps and desperate killers everywhere. The chance for the courier to get killed before reaching Vegas are many.
Why didn't he (as soon after the disk was found) send 2 dozen, armed to the teeth securitrons to retrieve it?

Second, as by wonder, the courier stands before him with the chip and what does he do? Offering a lousy thousand caps. Just give 250.000 caps or something. An offer that nobody would refuse no matter what other faction would offer.
But no, House threatens the courier to be killed if he/she doesn't hand it over. A well-armed courier (why wasn't asked to remove weapons like the other casino's?) that has been through hell to get there won't get him/herself killed by a few robots.

And after the robots are defeated, House just goes off-line. Why not make a second offer then? His whole life's work just to be ignored?