I would say go for it. Jupiter in Leo rules the MC, 5th house stellium, Neptune on the DSC. Transits are looking good too.
I would say that regardless of what your chart looked like, however. I've acted as a side project for a few years though I haven't done anything lately. There are all sorts of people who are successful actors. Coaches are supposed to criticize and they will criticize everyone; don't take it personally.
Re: shyness and social anxiety. This can happen for people who are constantly in their heads, analyzing life as they're experiencing it. It seems like you're one of them (as am I). You have to be more in the moment. Turn your brain off, so to speak. The anxiety will ease up as long as you need it to.