Richardson is my favorite city. I have family who live there, and I've considered moving there myself. As it is, I drive there several times per week to eat at my favorite restaurants, and I like the eclectic atmosphere. They have large trees in the well established neighborhoods.
The Dallas Area Rapid Transit Light Rail "Red Line" runs from downtown Dallas, through Richardson to North Plano.
http://www.dart.org/maps/printrailmap.asp
Richardson Arts
http://www.cor.net/arts.aspx?id=176
http://www.richardsonsymphony.org/
North Texas Swim Teams
http://www.ntswim.org/template.php?page=clubs.php
http://www.ntswim.org/template.php?page=athlete.php
Plano, TX (Just North of Richardson) - Aquaducks Youth Swim Team
http://plano.gov/Departments/parksandrecreation/Sports/Pages/aquaducks.aspx
Richardson schools are good. They have a lot of extra curricular opportunities for the students.
Plano ISD is one of the best in the state, and offers plenty of extra curricular activities.
Frisco schools are good, but lack the plethora of extra curricular programs that Richardson and Plano offer.
Allen, TX schools are excellent. They offer more extra curricular opportunities than Frisco, TX simply because the schools have been developed for a longer period of time. Frisco is growing by leaps and bounds, and the schools are having a hard time keeping up. Allen ISD ratings are some of the best in the state, but the number of programs do not match Plano and Richardson. Allen Band is the largest in the U.S..
Cross Timbers Youth Orchestra is based in Allen, but Plano, Frisco and McKinney youths also participate.
http://www.ctyo.org/
http://www.artsofcollincounty.org/
If you want your son to do better on his SAT scores, you should choose Plano schools. Their students' SAT scores blow other schools away.
Plano home prices range from affordable to multi-million dollar homes. Some people will say there is a bad area of Plano, but compared to many other cities, Plano really doesn't have a bad area. The West side of Plano is the "entitled" mcmansion side, and the east side (East of N. Central Expwy.) has cute smaller homes as well as nice, newer homes with large lots and plenty of trees. The East side of Plano also has two beautiful, huge city parks where they hold a balloon festival and outdoor concerts.
http://www.plano.gov/Departments/parksandrecreation/Parks/Pages/default.aspx
You will have no trouble finding a job as an esthetician any where in the area North of Dallas. People in this area are very "appearance conscious".
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If your son loves chess, he would be interested to know that the University of Texas at Dallas is actually in Richardson. UTD houses a nationally renowned chess team that has won numerous prestigious awards.
http://chess.utdallas.edu/accomplish.html