I think three times is enough - especially if it's about tries in the last 5 years. This is the information I see most often around the admissions forum.

I'm looking for a 700+ (I know I'll hit it sooner or later with my study regimen and progession).

I was planning on applying for schools this year (fall 2010) by the end of November (thinking of taking the GMAT mid october) but it looks like I'll have to delay it until next year (fall 2011) based off of my current GMAT score/ goal.

Do you recommend that I just take it anyway and apply this year just for the off shot chance that I'll make it into my choice schools? (my work experience looks very prestigious) Right now i'm only getting mid 500's on practice tests.

or

Do you recommend that I wait until I hit my 700+ goal then apply for 2011?

Thank you

It really depends on your target schools. I think this question should be asked in the admissions consultants section of the forum: they could offer professional advice on how to tackle this issue.

My top 5 schools are Tuck, Stern, Fuqua, Ross and Columbia. I talked to one of the admission officers from one of the above schools yesterday and according to him 3 or 4 times is the ideal. He said "no more than 5".

Thank you Dana and Bruce for your really helpful advice!