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Hi, Angela.
The first thing that struck me about the painting overall is that it certainly does have a "period piece" look about it. I can easily imagine visiting a "hall of founders" gallery, civic or religious, and seeing portraits like this. I think you captured that "historic record" aspect nicely. I trust that the painting was well received in the competition.
I'm reluctant to offer critique, per se, of a work that is "finished", but since you've posted for critique and will certainly be doing a lot more painting, I'll "jot" down a couple of quick notes.
The thing my eye won't leave alone is the dark gray "monolith" in the background, right. Whether it's a tree or the corner of a building or monument, or whatever, I'm having trouble accepting that it belongs there -- at least quite this emphatically -- either compositionally or thematically. I can see that there's a similar structure in the source photo, but there it blends into the "night scene" background as a whole, visible only through a slight lightening and the shadow cast by the figure. Since you've taken the "night" photo and created a "daytime" painting, it might have worked better to push the value of that structure much higher (especially as it rose toward the now-bright sky), to reduce its contrast with the rest of the background, and to increase its contrast with the figure.
Particularly in the close-up, I can't get past the feeling that the eye on our right is lower and closer to the nose than the eye on our left -- and yet my attempt to verify that through measurements fails, so I look for other explanations (including the possibility that I need stronger reading glasses). I can see from the source photo that the subject has an unusually broad and flat "keystone" area between the eyebrows that is creating some sharp-edged shadow areas ("sharpened" by the photography process) in the depression of the eye socket, making this a tricky feature to capture. Interestingly, in the source photo, the eye on our right actually looks (to me) higher than the other.
I think what it comes down to is that the eyes in the painting are, to my eye, generic, and do not partake of some of the strong, characteristic lines (especially the horizontals) of the eyes in the photo. Lastly, the presentation of the full pupil and nearly the full iris, coupled with the absence of shadow on the eyeball below the upper lid, creates the effect that the subject is looking down, rather than straight out of the painting.
Having mentioned shadow, I'll wrap this up by saying that I think the whole subject would have been stronger for some heightened modeling effects, using a wider range of values. The absence of dark values and accents is particularly notable in the face, hair, and shirt -- and in and around those eyes -- where their introduction might have resulted in more well-defined and dramatic form.
Seems too long for a "reluctant" critique, but I'll let you edit out the surplus. Again, the overall effect of the painting strikes me as well suited to the task you were on about in creating it for this competition.
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