To rent or not to rent.....that is the question

I figured to put this as a separate post even though it was related to the last one, but this is something that deserves its singular due.  To rent or not to rent...blah blah blah....the eternal question.  Does it pay to rent, does it pay to "throw" away hundreds of thousands of dollars on rent and not worry about fixing up a place that may not be to your standards. Or...do you plunk down a whole bunch of money on a place that you like now, but aren't sure if you'll like in 6 months.  And moreover, if you'll be able to sell it in 3-5 years when you want to move on. 
You see, in case you didn't know, living on LI ain't cheap.  Good luck trying to find a decent rental for under $2k a month...yes that is what I wrote.  It is the equivalent of a mortgage for a middle of the road house; nothing elaborate, just middle of the road.  No oversized tubs, no pools, no sprawling kitchens or backyards, just middle of the road.
Any ideas, any solutions?  Move out of NY you say? Move to a state with a cheaper economy you say?  Well, we tried that; 3 years ago we figure we would move off of LI in search of a "better life", a slower pace.  So we packed up all of our belongings, said our sad good-byes to friends and family and we headed south...to NC. This lasted 2 years, almost to the day.  The dh liked it at first, and I wasn't sure but once I got my bearings, I loved it....and he hated it.  First a little, then a lot; the disdain grew and it then became all about moving back.  We rented an apartment (actually 2-we moved 8 months after we got down there); figured we would rent while we were looking for our "dream house"- or at least our starter dream house. Sure, we almost bought a house down there that by LI standards would have been 2-3 times more expensive here, but no sale.  But that's a whole other story, for a whole other blog....maybe another time.  So again...we packed up everything we had and headed back up to LI.  And then the questions began....do we rent or do we buy??? The dance just keeps going and going.  And this is where we stand..