When I first looked at Hayate no Gotoku, I definitely didn't expect it to be a show I'd end up enjoying. Just look at the plot: a boy goes to work for a 13 year-old girl as a fighting butler in order to pay off his debt. Then there's the whole stupid romance aspect, a talking tiger, a cross- dressing Hayate, flat characters (I'm not talking about Hinagiku), and a plot that NEVER advances. On paper this should spell disaster. I mean, if a show like this took itself seriously, even for a second, there's no way it could work, right? Right. Good thing it didn't.
Let me say this right from the beginning: if at any point I felt that this show was actually going somewhere with the plot I would have jumped off screaming. However, it is at a literal stand-still throughout the enti re show. Hayate is always in his stupid situation as a COMBAT BUTLER!!! and Nagi always has her silly crush that Hayate will never ever pick up on. The characters also never develop past their initial...characterizations WHICH IS A GREAT THING. Why is this all a good thing? Let me explain.
With all of the pesky things like plot and characters out of the way, this series can simply stick to its guns throughout its entirety: being freaking hilarious. The characters and plots are simply used to carry references, absurdity, parodies, and other assorted jokes with no regard for anything else. What this makes is for a show that makes you laugh. A lot. Typically, that's what I look for in comedy, with the romance bits only being there to create more comedy, and when drama is introduced it immediately gets shattered for more comedy. And when you finally think two characters may realize their feelings for each other something goes wrong for more comedy.
More shows need to be like Hayate. We have plenty steaming piles of crap out there whose biggest flaw is the lack of being able to tell a good story. Usually, this is because their premise is horrible. When the premise is bad, generally trying to tell a story won't work. So, shows, instead of trying to make it work, simply create intentionally bad premises for comedic purposes. Use 1-Dimensional characters as segways for jokes, and if you ever feel the urge to advance the plot, make sure it's only done for the lols.
At the end of the day what we're left with is a show vastly superior than the sum of its parts. If you need a story to keep you going through a show, then stay away, but if you can lean back and learn to just take everything for what it is and laugh, this should be a treat.