No, I think he will ally because he wants humanity to progress. Progress is kind of Mr. Houses thang.
Mr. House explains to you how he's not a war-hawk with a big ego, like Kimball, General Oliver, Moore and Caesar. Mr. House won't go to war with Caesar's Legion because he doesn't need to. He only attacks others when it's to save New Vegas, or to save himself. Any other war will be a waste of resources and securitons and he'll have nothing to win. Of course, if I would be the head of Caesar's Legion I would have a lot to win if I'd decide to attack Mr. House. But for the sake of progress, I let Mr. House in control over New Vegas, and ally with him.
It's highly possible, however I think it would be tough to convince him at first, the man would likely think you're attempting to manipulate him, though a show of good faith regarding his securitron army would probably alleviate that fear my main concern would be the changes with the Legion itself.
I think there might be difficulty with them accepting such a radical overhaul, though perhaps I underestimate their devotion to the Caesar.
The Legion have excellent discipline, once they see you as an equal they're very polite and well dressed is a matter of perspective, they're better dressed than most wastelanders but I think while NCR uniforms are generally untidy they do look better.
Of course, we can argue that their kindness when they see you do well strongly infers their group mentality defines their kindness, so it's up to how you define well mannered...The White Gloves strive to be well mannered...