Well I think in so far as overall location combined with schools and shopping Alamo Heights is tough to beat in overall accessiblity. However some of the other neighborhoods "inside the loop" have amazing private schools....
North of 1604 is all new construction, whereas "inside the loop" classifies neighborhoods like Alamo Heights, Monte Vista, Olmos Park, Tobin Hill, and King William. Here you will find older, or historical- quality architecture, loads of trees, inviting street-scape, and tons of exciting things happening as the urban area is quite "switched on.".
And too, "Inside the loop," there is ample supply of art and culture, foodie-fun, friendly, lively, city, re-development, urban action, close to downtown and the evolving riverwalk.. I would think being from the city- you would gravitate to these areas?
If you want to do something COMPLETELY different and go charming, quaint, "country," look at New Braunfels or Boerne. They still offer proximity to a variety of locales of all genres... Certainly proximity to any commutes may help you to narrow it down. There are a ton of great things happening all over the city, and it is the hill country-beautiful in many areas.
Feel free to contact me directly if you would like anymore feedback, or if I can help in the transition, (a big one :- ), in any way.