Hi Mikell,
I think we can all sympathize with you on this one. Unless you happened to have won the TG genetic lottery or are still very young . . . well lets just say, skin doesn't stay where it should after a certain age and it doesn't matter if you are a GM or GG. Added to this is our zeal to appear "feminine" which once again is difficult as we are guys with guy facial features, beard shadow and what not. Not trying to be a big downer but it is true. However, we also tend to be our own worst critics when it comes to how we looks as we scrutinize every aspect of our job. I asked my wife when I first started going to be brutally frank about my appearance and she has never held back. So imagine my surprise when I thought I did a great job I get the "not good" and vice versa when I think I did a bad job I get the "thumbs up".
As others have said "less is best" but then again that holds if you have limited facial hair. Hiding dark beard shadow is an art form and sometimes a quick shave, a bit of red, light foundation won't cut it. So we end up with multiple layers. I think where it goes wrong is blending up into the areas that don't require foundation (e.g., around the eyes) . . . here I find concealer matched to the foundation works best as it does not appear cakey. However, the one thing I have learned is that if the make-up is natural looking (within the confines of what we can do) most people won't bat an eye when you go out as they are not studying you in close detail.
Hugs
Isha