I honestly hate the term "women of color" also. Everyone has a color! At what color do you run into unique problems because you're darker (that women who are freckled/tanned/pale/etc. don't also have)? I don't know what would be a more appropriate term.
Moving on...I always had a hard time finding a good foundation match at the drugstore - I overcame that pretty easily by getting myself to a dept. store where they were matched me. I ended up going to MAC and they happened to have an exact match (NC45). I do have a fairly common shade and had access to a dept. store- for those who don't, I can see why finding a good match is so difficult. My "summer tan" also doesn't pose much of a problem as I just avoid foundation during the summer, but I'd guess that most other women have similar summer makeup issues.
I dislike that sunscreens with physical block ingredients make me look very gray, but I just use products whose primary ingredients are chemical blocks. It's the nature of sunscreen - physical blocks are just that color, I don't know of any way to get around it. Though Lord help you if you're one of the few people you react pretty badly to avobenzone! Like Mac_Pixie04 I'm also wary of getting mineral makeup because it tends to go gray like sunscreen.
Since I'm southeast Asian, I have pretty full lashes/brows/etc. My lashes are very straight though, so it took me many years of trial and error to find a good mascara and lash curler that worked together.
And just like Beauty Mark, I've had a lot of difficulty finding a "neutral" or "nude" lip color. I still haven't found one that is not too pink or brown and also works with my 2-toned lips (upper is darker than lower).
As for issues with limited recommendations from makeup artists, I don't frequently go to dept. stores or counters so I don't have too much experience with it. However, on the occasions I have gone, they haven't been limited in their choices for me at all. I've been told I could wear most colors, and I know it's usually my reservations that prevent me from doing so.