From here, you essentially do the same exact endgame sequence of events as you did for your play through of 'The House Always Wins,' with limited change in dialogue.
Which I'm assuming you'd have to do to get the endgame question anyways, all you need to do is talk to Yes Man and get him installed onto the Lucky 38 computer. Upgrade the Securitron army under Fortification Hill House quest line up until this point, that being: Assuming you have done everything correctly for the Mr. House (use the terminal to the left of his big screen). House and a large warning message pops up asking if you are really ready for the endgame), you have saved yourself a ton of time.
House to the end, thus getting 'The House Always Wins' and 'All or Nothing,' AND if you have a game save just prior to accepting the final quest at Hoover Dam (when you talk to Mr. If you have done the main story and followed Mr. A very easy way to nab this achievement (along with Wild Card obviously)