I have lived here since I graduated in 1989. I am also from a real small town of a 1,000 or so. The short answer is I love Houston and would hate to move.
A few suggestions if you've never spent anytime here.
1. Like any big city, traffic is bad. Unlike some big cities, don't count on any help from Public Transportation and walking is not an option because the city is spread out- plan on driving everywhere.
2. If you have a family and schools are important, look at the school districts outside of the city. I live in Sugar Land which is Fort Bend ISD. There are several strong school districts circling 3/4ths of Houston. I would stay away from the East Side unless some other Houstonians have some suggestions I am missing.
3. If you don't have a family, try to live inside the loop. A lot of the night life is centered around the Washington Avenue area but their are many, many advantages of living close in. Personally, this was my favorite area to live.
4. The weather sucks - We have too seasons - Hot and Too Hot to be Outside. Winter might last 3 weeks in a cold year.
5. Cost of living is cheaper in Houston than many other major cities, especially housing. Its way cheaper than the LA, NY's and Chicago's of the world. Look at what say $150K-300K will buy you in Houston vs many other cities. You can get a good house in a great neighborhood.
It's a great place to live but like any city it does a few inconveniences. As the other posters, PM me if you want more thoughts.