Recommended towns in Virginia

Don't know what it costs anymore, but I like Fredericksburg. There's an express train to DC where you can take a plane or Amtrak to NY or wherever. It has a cute little old town. All of NoVa is pretty good for its adult ed and parks and recreation departments. Ok, maybe I'm generalizing. I haven't been there in a while, but we visited about 4 years ago and I thought it was lovely.

Richmond has also gone through a little renaissance. There' s a small town just outside -- Petersburg, I think -- that for a while was giving away houses to people who would fix them and live in them.

Don't know much about the beaches. Maybe somebody else will come along who knows more.

Good afternoon, whiteviolet, from realjohnboy in Charlottesville, Virginia. Here are some thoughts. The northern Virginia suburbs of D.C. would work on most counts except affordability. It is pretty much an urban sprawl which appeals to some.
Charlottesville is home to UVA. Excellent in all categories plus a top notch hospital to boot. You didn't mention that as being potentially important . More bookstores and restaurants per capita than most any other place. Lots of cultural stuff and adult education opportunities. Public transit within the city is pretty good and getting better. Air and rail N-S and E-W is pretty good, although you might have to transfer in DC, Atlanta or Cincy.
Affordability is an issue. You did not define the word, but things are not cheap here because of the overhanging student market and too many high listings on the "Best Place to Retire in America." I can tell you that "someone" I know has a cute 5-unit townhouse property with high-end 2-BR, 2.5 baths on a nicely landscaped area 4 miles from downtown with public transport for $1200/month.
I would also suggest looking at the Blacksburg-Roanoke and Harrisonburg areas. Both have universities and community colleges. I would guess that they are perhaps 10 or 15 years behind C'ville on the "cultural events" scorecard. They rank pretty high, higher than Cville, on the affordability meter.
I can't talk about the coastal area if your friend is an ocean fan. Pretty urban.

I hope this helps.

Thanks for both these comments - really useful.

He intends to buy and is reasonably well off, I gather, but hopes to save on current housing costs (has a luxurious 5 bed house in Oregon but only needs a more modest 2 or 3) and hopes to save a bit on housing in order to travel. I was reading about Charlottesville myself - sounds lovely! He loves bookstores and restaurants too! I shall look forward to any more observations with great interest.

Thanks again, both of you.

I love Charlottesville and planned to retire there until I got the bug to move to New Orleans. I still may retire there if living in NOLA doesn't turn out to be what I hope it is.