Most schools don't look negatively on 3 attempts (or fewer, obviously). Some schools care about more than 3 attempts. In some cases, the school doesn't have an official policy and it's up to the individual admissions officer.
Also, there's a difference between taking the test 4 times in the last 8 months vs. twice a couple of years ago and twice again this year.
If you're concerned about the issue, you can contact the schools in which you're interested and ask them if they have a policy about re-takes or what they look for when someone has taken the exam multiple times. (You don't even have to specify how many times if you want.) If you do this, make sure you are polite and business like. Also, proof your email (use spellcheck!). The way you present yourself will be remembered if you apply!
I did hear of one extreme case (well, I thought it was extreme). An admissions officer told me that he looked down on a person for taking the test twice, specifically because the person got a 700 the first time. He thought it showed a poor sense of priorities that the person would take the test again after getting a 700. (And, I guess I can sort of see his point - there most likely isn't a great reason to take it again after that - but I don't know how much I could conclude about a person's sense of priority just from that. What if some other school asked him to take it again because they thought one of his subscores was too low or something? Anyway.)
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Stacey Koprince
GMAT Instructor
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Manhattan GMAT
Contributor to Beat The GMAT!
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