there is no way around it. There is an excellent subforum here on J-1 and HRR. Do read up on the topics in it.
You can file for AOS after you get the waiver. Definitely NOT at the same time.
In some cases (no objection waiver only), you can apply for AOS with a copy of a favorable recommendation from Department of State. DOS forwards it to USCIS which in turn opens a I-612 case (the actual waiver). This way, it looks like both applications are made at the same time, although technically they are not.
DOS sometimes (in my case, for example) requests proof that that a person had been in the US legally the entire time.