Not sure what you want waived...the TSA requirements have nothing to do with pilot medicals or pilot certificates. The TSA only comes into play when you apply to work at an airline. I'm am very certain that that requirement is NOT waiverable under any circumstances...what you would need to do is see if they even count juvenile offenses, or try to get it expunged. An expungenent should work for TSA I think. If it does count against you, then you will need to work as a CFI, corporate, or possibly 135 pilot until the ten years is up. I'm not sure if the TSA rules apply to 135 operations?

If you are looking to waive the requirement for a first class...well, they evaluate each person on a case-by-case basis anyway. It depends on the nature of the crime, your age, how long ago it was, and your attitude. They may also require a physcological exam to make sure you don't have "issues" which might have led to criminal behavior. Once you overcome this hurdle to get a first class you will never again have a problem with it on a medical...best to do that before you spend money on training.

But, yes talk to an aviation lawyer who has done some aeromedical work.