I was opposed at first to my DD having a personal para for the same reason, she certainly didn't need a shadow. I was assured she would not be escorted down the halls and the para would look like a class para but DD would be her primary responsibility. Other parents have told me this scenario worked out well for them. I guess it really depends on the players.

If they hire a para specifically for your DS s/he can and should be trained on his specific profile. Due to confidentiality concerns the school gave only very limited info about my DD to subs or other teachers who did not work with her regularly. We were told that a part time para could be hired specifically as a match for DD's needs. The first one they hired often didn't show up for work which created major issues since the teacher refused to modify or accommodate DD when the para was out. She was replaced by a fantastic woman who really got DD and was super supportive. She couldn't handle the hostile environment and also left. This was when they offered a full time para. Unfortunately as a full time positions it was opened as a transfer opportunity to anyone in the district - no ability to screen for a proper match. They ended up using several people from a temp agency with very mixed results.

I guess you have to decide on your primary goal here. A dedicated para will mean no more begging for scribing, will support his AT use and can be an extra set of eyes and ears for you if you can trust them enough. If handled properly there shouldn't be a stigma. No way to know in advance, though, if it will be handled properly.

In our case the district folks would all decide in advance and then recite from their script at our IEP meetings. This meant that even if we were there we would get blindsided and we or our advocate would have to think on the spot of the right questions to ask to try to figure out if we did or did not agree to some thing.

This shows that you have them flummoxed Irena. It may be that a para is the next step towards that OOD you were asking about recently. This may be their make it or break it attempt to show they can/can't meet his needs. It also makes their cost for in district vs out of district less lopsided. If you accept the para and your DS still has trouble accessing his education you may have a clear path to that LD school you recently mentioned.