I suggest trying a back to back comparison.
Find your regular low cost massage therapist that gives a great massage. Ideally this will be a person with training (e.g. Cindy the backwalker in Flushing). Then, go to a higher end spa (e.g., spa at a top hotel like the Mandarin Oriental, or a private practice in a large city like Philadelphia, etc). Be sure to request a Certified Massage Therapist (CMT).
You will pay 3x to 5x more for the high end environment. Some places include private pool time in advance of a massage, and you can include a partner which is nice (thinking of a few places in the Hamptons, but it is common). If you have a specific ailment, inform the CMT, and they can offer relief based on their knowledge of skeletal and muscular structure.
More times than not, you will get more frequent massages with the lower cost skilled therapist that is more available and will get to know your body with regular visits. I find this to be more practical because they are more available than a CMT on average.
I personally enjoy both.