Hi Chris. First, I think that while some people will already have a leg up on the "it" factor when they first start art, I think a very big chunk of artists develop it as they put in the hours making art. I also think it's important to note that even with artists who have great acclaim, they also have varying success and emotional reactions between their different pieces. I've heard quite a number of artists on different podcasts, youtube videos, and articles comment on how people will go crazy for certain images they make, and other images they make won't get that much of a response, even if they are expecting it to. So this seems to be a general artist problem.
Addressing the different reactions between your two portraits- my guess is that the lighting of your reference photo and the expressions of your subjects had a lot to do with the different responses. It being a tribute to a deceased loved one, might also have been an important factor in the response. If you made many many more of these portraits, some would get better responses than others. The same would be for the best portrait artist in the world.
Now addressing your work in general, what I see from your work is someone who likes to jump around with different styles, subject matters, and mediums, but does not spend a lot of time with anything specific. (I tend to do the same thing
) As a result maybe you haven't put in the hours and focused thought that a lot of people with the "it" factor have. They may have started off playing with different things, maybe even for a long time, but at some point they shifted into buckling down and narrowing their playing field and they started tons of more focused work, a lot that they might not even show anyone. Lot's and lot's of sketches and/or finished piece. Tons. They really hash out ideas, subjects, and mediums. They probably have made a lot of not so great art in that process. Yes they may explore with different things and may not exclusively stick to the same things, but they have put in the hours to know how to manipulate their work in certain ways, and can focus more on emotional impact.
Just from your instagram, I think I identify 10 different mediums you use (watercolor, marker, pastels, charcoal, graphite, oils or acrylics, colored pencils, digital, mixed media, ink). You use them in different styles and in different ways. Since everything seems so spread out between subject, styles, and mediums, I wonder how much time you've actually spent on any given one. I think if you did a 100 challenge and limit your subject matter and medium it would teach you a lot.
I hope that wasn't too harsh, but you seemed to be looking for honesty. I could be totally off base, as I don't know your history or how much focused art you've actually produced. Interested to hear what others have to say. It's an interesting subject for sure.