The fact that the reapplicant essays are the same as the first-time essays (just like HBS and Stanford) tells you something -- that they view reapplications as if they are first-time applications. They aren't going to be referring to your prior year's app (they don't have the time) and the fact that they don't ask the "how has your candidacy changed from the previous year blah blah blah" when they asked that in prior years should also tell you that they don't want to hear it. If they did, they would've asked - they omitted any reference to that pretty deliberately.
Also, using the failure essay to talk about how not getting into Wharton was a "failure" can come across as needy and pathetic. Think about it. It's the same kind of "blech...." response you may have when some guy you went out on a date with tells you "the worst day of my life is when you told me "lets just be friends", so can you give me one more chance to prove you wrong?"
I really don't have any "general tips" (I'll leave that to my competitors) since following a bunch of 'general tips' usually leads to cookie cutter essays.
Essays don't have to be perfect or polished. It's about being authentic and individual. The essays have to be written in a way that only you the individual could write it, even if you are covering some of the same themes as other applicants. Every applicant is different, if they choose to see themselves that way and have the confidence and imagination to express themselves that way. That's basically what I do with clients - every one will work a different way.
Some people have a very dry sense of humor. Others are sprightly. Others have a quiet quirkiness. And yet others are really in-your-face but in an engaging (and not intimidating or aggressive way). Some are contemplative and meditative. Others have a wicked wit.
B-school admissions has gotten to the point where there are so many people now who are comparable in overall caliber. Lots of people with similar resumes. Some get in, some don't, and what separates the two often comes down to a bit of a personality contest (i.e. it's not what *kind* of personality, but the difference between showing *a* personality than *no* personality).
A lot of the applicants I've seen in past years that had trouble getting into schools where on paper they should've been competitive for, often comes down to a lack of personality in the overall application.
Adcoms aren't bullsh*tting when they say they really want to get a sense for who you are as an individual. They have to wade through so much God awful boring and dull essays, uninspired interviews, and generic rec letters that could've been written by a bot that it really comes down to whether they remember you or not. Working in a corporate/business/office environment has this amazing way of completely sanitizing one's communication style -- bland may work if you're in a "cover your ass" environment, but in b-school admissions, bland usually means a ding.
And that does mean taking some risks. Being yourself in a more *authentic* way forces the adcom to form a strong opinion of you -- good or bad, but that is certainly a risk worth taking when the alternative is *no* opinion (which is the same as a ding).
Also, there's a difference between being gimmicky and being original -- the former isn't "authentic" but is a byproduct of neediness and desperation (you'll do something wacky just to get noticed). The latter comes from a strong sense of self-awareness - knowing who you really are beyond surface level stuff and what makes you who you are. You can still have a conventional resume with nothing on the surface that makes you much different than other applicants, but still be an original and unique individual -- if you know yourself well enough to be able to convey that.
Think Coke vs. Pepsi, iPhones vs. other smartphones, or different cars in a similar category. You can microanalyze the specs to decide what makes them technically different - but most people choose based on how they FEEL, and that is a complex and ambiguous mixture of factors, but the companies spend a lot of time and effort figuring out HOW to get these consumers to feel a certain way.
A lot of applicants will microanalyze their profile to death, but the fact is, adcoms will choose people similar to how consumers choose consumer products (a mix of interrelated and ambiguous factors both rational and emotional). The applications process is basically a BRANDING exercise. The brand is YOU. You're trying to convince them to pay more for your Coke or Pepsi (and not the generic stuff, even though they basically all taste very similar and have the same ingredients).
And yes, that is hard - because there is no hard and fast *process* to do this, and there's no cut-and-dried opinions either from an adcom's standpoint (some may like you, some may not like you no matter what).