I moved to Ithaca from another part of upstate New York. The community has a strong college town vibe, since it is home to Cornell University and Ithaca College, each on opposite sides of the city.
Ithaca itself is really quite an interesting place. It's tucked away in the hills- the nearest interstate is 25 miles away, and the nearest major city is 60 miles (Syracuse). Weatherwise, the summers are warm to hot, but fairly pleasant, and fall and spring are mild. Winter is definitely a test for those from warmer or sunnier climes. Being on a lake, and close to the Great Lakes, Ithaca is often walloped by clouds and snow, and temperatures only average a high in the 30s in winter. If you can handle the clouds in the cooler months, and the rather gloomy winter, then you should be fine. The gorges and waterfalls are stunning, and there's quite a bit of natural beauty to the area.
The people of Ithaca are an odd bunch. You'll find hippies on the Commons, a Buddhist monastery being built on the outskirts of town (the Dalai Lama has visited a few times), intellectuals and college students near the campuses, and traditional upstate conservatives in the suburbs and rural towns nearby. An ecclectic mix by any means, but people still tend to place a lot of pride in the community and in the region.
I've never had a problem with shopping personally. Big box retailers (Wal-Mart, Target, Best Buy and Kohl's to name a few) can be found on the flats in the southern part of the city or the northern suburbs, and mom-and-pop stores and small shops are abound in downtown. The result is a fairly healthy mix of local character and afforadable national chains.
The economy is primarily colleges and tourism, with some high-tech businesses and traditional manufacturers mixed in. The area used to have several large factories, but as unfortunate luck would have it, they shipped out (one of the largest employers made typewriters---the computer age shut them down). Although the economy is growing, it is slow growth, the area is still small in population, and high-paying jobs can be tough to come by. Affordable housing can be hard to find in some parts of town too.
I have never been to the ICSD (Ithaca City School district). but with education being such a major facet of the economy, you can bet it has high standards. It's on Newsweek's lists of top schools year after year, if that suggests anything. Healthcare (Ithaca is served by Cayuga Medical Center) is pretty decent.