Don't know anything about Chesapeake, but all the other cities are in NC and will have the same state taxes. Wake (Raleigh) has the lowest property tax rates of the NC cities. It's followed by Forsyth (Winston-Salem) @ ~28% higher, and then Durham (Durham) @ ~30% higher. However, Raleigh will be more expensive for purchasing housing followed by Durham, then Winston-Salem. Since you say that you'll be renting, I don't think that you'll have a problem finding rentals in any of them under $1500. Age of property, amenities and proximity to each downtown will drive pricing. New, amenity rich, buildings in DT Raleigh and Durham will exceed $1500 for sure. I suspect that the same will be true for W-S.
Sales taxes will also vary among the cities with Durham having the highest at 7.5%, Raleigh second at 7.25% and Winston-Salem at 6.75%. All are based on the same 4.75% state rate with local taxes levied on top of it and subject to change.
Since Raleigh and Durham are next to each other, many of the things afforded to one will be accesible in the other. School performance is generally better in Wake County than in the other two counties. This is based on overall data, not specific school performance. Chapel Hill schools perform the best in the state and are to the immediate west of Durham, but it's also more expensive to live there. Wake's schools are rated 5th best in the state followed Forsyth (15th) and Durham (38th).
https://www.niche.com/k12/search/bes...orth-carolina/
Given how fast NC has grown, finding a planned community will be really easy. This is especially true in the Raleigh-Durham area where growth has been huge.
Raleigh is nearing completion on a new Amtrak station downtown with continuing work on its connecting corridor to the NE and toward the west.
Don't know about the food scene in W-S but the Triangle has had a lot of accolades for dining, James Beard winning chefs, etc.
The traffic in Raleigh-Durham will be worse than it will be in Winston-Salem just due to it being a more populated area.
All NC cities are near lots of outdoor activity options and state parks. W-S will be closer to the mountains and Raleigh will be the closest to the coast but none of the cities are inaccessible to a wide variety of options.