If you wear earrings, def wear plugs. Girls also gauge their ears, but tend to do so on a smaller scale. I find that somewhere around 00 is a good masculine size without permanently stretching your ear. That's where I'm at now, but I won't go bigger because of job related concerns. It's all a style thing, and yeah I think you can make it work as long as you're not too clean cut, especially if you keep your hair shorter.
Most guys don't look good with my buzz cut (I know I don't) but you pull it off well in this pic. I don't think the shaving is really doing much for your passing. Lots of guys emphasize shaving the fuzz, but I'm 7 months on T and have only shaved like 3 times. But maybe as somebody mentioned, guys with darker hair need a bit of that shadow to help pass- and my fuzz does exactly that.
Who knows why you don't pass. You may just look too young in the environments you're in, so they assume female. That's what happens as you get older, you pass less.