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Right, so if you move to Chesterfield with a 5 year old, and the house you buy is an area that goes to X elementary school, which feeds X middle school, which feeds X high school at that time, the county cannot later make all or part of X middle school feed Y HS because of change in enrollment or population distribution......
...because you said so?
No not because I say so You can choose your High School and Middle School but Elementary is harder but can be done also, I see it all the time. It's not like L.I that feed into zoned schools. But after 5 years of living here, I'm sure you know better than I
Central VA is quite nice with a lot of great schools in areas that are affordable compared to LI. There are a lot of really good IT jobs & salaries in DC and NOVA, though you can do about as well in Richmond if you find the right company. Also a lot of very good hospitals in the Richmond, Henrico & Chesterfield area.
I agree with other posters in that 1) make sure you can find a job, 2) get a feeling of the lifestyle, atmosphere, and offerings of the relocation areas before moving, worst thing you can do is move somewhere without doing your research, those are the people I notice who are unhappy after they relocate.
Don't worry about schools because you can find great schools and bad schools everywhere. I'd rather send my child to an A school in Florida than C, or even B school on Long Island.
The most popular relocation states in the south amongst Northeasterners are Florida and North Carolina as you probably know, and now Virginia, South Carolina, and even Tennessee seem to becoming more popular. I only lived in Florida a short time but I actually do like many of the cities there, medical is pretty big there but I'm not sure about IT.
Colorado and Arizona are becoming popular relocation spots in the west. Low housing costs and taxes, nice weather, Denver and Phoenix are good cities with a lot to offer. Medical jobs are good in both states. I heard that IT job market is decent in Phoenix, but you're better off talking to someone in the field.
I also hear Austin is a mecca for IT, but again it's better to talk to someone who has actually live there and know the field.
Now I know this may not fit all your criteria and probably not what you've been thinking, but you may do well in California. We all know there is a great IT market in the Bay Area, and also a good market in the Irvine SoCal area. Yes, California has high housing prices but IT salaries there generally pay much more than NY, most CA property taxes are bargin compared to NY, fresh fruits and veggies are cheaper there, and energy costs are minimal because of the year-round temperate climate. Also housing is much newer there than Long Island, so while you may have a high housing costs you most likely won't have to invest in many renovations. The biggest problem is probably the fierce competition in the California IT job market. But if you can land a well-paid IT job there it's definitely worth it.
Good luck with your decision.
I just recently retired and we are heading to Sarasota and I have extensively researched the schools down there and we are sending my daughter to a private school...an A rating in Florida doesn't mean anything, pick 3 difft schools and you will get 3 different test scores on the fcats but yet they are all still an A ??? Why, because in the state of Florida they can only move a school one letter grade per yr, most of the schools in Sarasota have a good reputation and are far better than most of the state. To say not to worry about schools when you move is not fair to someone who is planning to eventually have kids, they will need those schools. You can go private but then it is usually expensive and will end up costing the same if not more as LI , taxes are lower but the schools are much worse, generally speaking. You can build a new 3000 sq ft home in Florida for 300-400k, at least in Sarasota, taxes will be about 3,000 a yr, you can be in a gated community, neighborhood is clean and only have to deal with the snowbirds every once in awhile. 300,000 here gets you a 2000 sq ft home with 10 k in taxes, also a state tax, and it will need probably need some work done. Sarasota as well as Florida has a need for the medical field, no idea about IT, and you will be minutes away from siesta key beach and Anna Maria island, 2 of the best beaches in the country as per travel magazine. Oh, and you don't have to shovel sunshine !!!
My husband and I are in a similar bind ... we can't afford to stay, we don't want to leave. We located an area of PA with superbly rated schools and a much more affordable cost of living. Only about 2 hours from where we live in Nassau County. Horsham, PA.
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You can choose your High School and Middle School but Elementary is harder but can be done also, I see it all the time. It's not like L.I that feed into zoned schools. But after 5 years of living here, I'm sure you know better than I 
