For me it comes down to a choice. You can seek out and dwell on negative stories and define your son's life by pain, pity, and fear. Or, you can decide to approach life with a strong sense of appreciation for many gifts he has and with an openness to allowing him to develop a positive sense of self which includes both an appreciation for his own capabilities and trust in the kindness of other people.
The more you put out this negativity the fewer kind and supportive people you will draw into your lives and the more isolated and unhappy you will feel. To me it makes sense to balance risks. There is a 100% guaranteed negative outcome of making your child fear other people and feel like he has to hide who he is and what he needs and that he can't have age appropriate independence but instead needs his mom by his side at all times hovering and monitoring. That is the road to depression and anxiety - which often play out in the form of physical pain, headaches, and sleep disturbances.
Yes, if you encourage more independence sometimes it may not be perfect. Perhaps there will be an insensitive remark or perhaps someone won't understand. It is not the most likely outcome, but a possible one. That is something ALL parents need to face as their children are on the road to independence. At the same time allows him to develop in an age appropriate way and be confident enough to become an independent person. It allows him to develop resilience and the ability to advocate for himself. For me it makes no sense to choose a guaranteed negative outcome over a path that offers huge positives with small possible negatives.
"My son and I have talked about it and right now he would rather have people think he has a helicopter mom until he gets used to the pain. I have not seen anyone else on any message board with a smart sensitive kid who has to learn while dealing with daily pain."
What you may be overlooking is that his pain may be intimately tied anxiety and that helicoptering is feeding that. The mind-body connection is a powerful one. I would suggest looking at the long term goal and working backward. If you want him to be independent on a college campus at age 18 how do you see that happening. Let's say his pain can't be resolved, is he to just let go of college or will you come with him?
As far as people on the board with smart sensitive kids with disabilities, you may be surprised. There are many kids with medical problems, including hypotonia, who are MUCH more affected than you are describing but they go on with their lives happily. We've pursued all sorts of approaches here (occupational and physical therapy, setting small manageable goals and working toward them, supplements, work with a psychologist, biofeedback, relaxation exercises, orthodics and shoes, conventional medical treatments, lifestyle choices like limiting screen time and having calming routines, daily strengthening exercises, building a supportive network of friends, and connecting with the disabilities community where we are forever reminded that our lives are a walk in the park). Yes, it all takes effort and work. It isn't always easy. But, that's life. You do it because the alternative is far worse.