The skin tones will be significant so I hope to get a hand up with a color checker. And I agree, color calibrating my monitor is less interesting to me and I’m leaning toward the color checker alone, and perhaps using a cell phone image as an auxiliary guide too. It would be interesting to have a phone image side by side with a Portra image to check the numbers on the skin tones.
I'm not sure the ColorChecker will help you that much. What I would suggest, given that you seem to be a committed photographer, is to bite the bullet and learn how to work "by the numbers," at least to some extent. To me, the way to do this is to learn how to deal with CIELAB numbers. (Forget about RGB numbers; they mean different things depending on the color space/ICC profile in use.) In CIELAB (aka L*a*b*, or on the internet typically just LAB) the numbers will always keep the same meaning. (They are based on a D50 light source, as i recall, which is loosely the same as daylight with a color temperature of about 5000 K.) Plus they vary mostly in agreement with human perception.
CIELAB is probably not easy for a color photographer to jump to. You were probably brought up on the idea of red, green, and blue being mixed. In CIELAB you have to deal with two sets of "opposing" colors. All of the color info is in the a* and b* values. a* is essentially red vs green, and b* is yellow vs blue, with zero value being neutral. The L* value is loosely brightness - zero is black, and 100 (usually) is equivalent to a perfect white reflector.
When you deal with daylight flesh tones they're gonna fall in a fairly narrow range of a*, b* values. Typically about 18 to 20 with equal values (these are roughly what the ColorChecker flesh patches will come in at). Higher numbers are a more saturated color, lower numbers are less saturated. If someone has a ruddy complexion the a* value will be slightly higher with respect to b*. Or if a yellowish complexion then the b* value will be slightly lower with respect to a*.
You mentioned the possibility of greenish skin. This will be the result of a* being low with respect to b*. For example, say you have typical forehead flesh values of L*, a*, b* = 75, 18, 18. If you wanna turn the skin slightly greenish (seen more as a lack of red) change the numbers to roughly 75, 12, 18. For even more try perhaps 75, 6, 18; this ought to give a good sickly green skin appearance (although green is not actually present, only a lack of red). For real actual green the a* value must go negative, for example L*, a*, b* = 75, -6, 18. (This is actual green mixed in with a good amount of yellow.)
If you are willing to spend the time to learn how these numbers work you shouldn't have any more trouble recognizing bad skin tones. In case you don't know how to get CIELAB numbers... you mentioned that you use Photoshop. As I recall, in the window that shows pixel values you have two readouts. I would typically leave one in RGB, then set the other to LAB. (I presume that normal Photoshop still does this.)
One disclaimer: CIELAB is based on a more or less normal lighting situation (as I said I think a D50 illuminant). If you are trying to do something different, perhaps to give a yellowish tone to suggest a sunset or colored lights at a concert then these aim values don't apply.
FWIW I've spent years and years dealing with color problems in photo labs, and have made hundreds of ICC profiles for digital cameras. Hundreds and hundreds of printer profiles. (In those days i/we used the more expensive Macbeth SG target, something like 140 color patches, as well as its predecessor.) So I'm speaking from some experience when I suggest taking up CIELAB; it's what I would do. But... it's a considerable learning curve so it's not for everybody. It's just a matter of what it's worth for a specific person. Most serious photographers (without a lab guy) would probably profile their monitors (using a hardware puck/software) and work visually. So they don't need to learn numbers. But if your color vision is an issue... well it might be worthwhile. I dunno.