I'm a 92Y and my window is opening up on Aug. I would like to reclass into a medical MOS. My question: is the BEAR program the only option to reenlist and reclass? Or can I just tell the Career counselor the what MOS I want to reclass into?

Because your MOS is understrength, you cannot extend under the BEAR Program ... you can reenlist for Option 3, Army Training Reenlistment Option.

So does that mean that if I check the in/out calls for any MOS that I qualify for and as long as there is a shortage in my grade/rank SPC(P) for the MOS that I choose, I can
reclass in that MOS?

Not any, but you'll need to get with your Career Counselor and see the MOSs that are offered to you basd on your qualifications. Occassionally, you can get an MOS that is shortage and not initally offered. This is based on the current and projected strengths of the requested MOS.