Hi Patrick,
It sounds like you did this painting a while back. Is that correct? Are you still painting? I think you did a great job, considering you were recovering from some major injuries. I wonder how the same portrait would turn out now, after recovering from those injuries?
I too like the addition of the flag and the wooden wall. It really adds character to the portrait. There's something about the American Flag that just stirs up all kinds of emotions in people. Great choice!
You made a great attempt at the sheriff. Since this is a portrait artist's forum, I'll try to give an objective critique. The portrait of the sheriff is stiff. If you think about it, it's kind of funny because at the time, you probably were very stiff yourself because of the injuries
It makes sense that this would transfer over to your paintbrush.
When you compare the painting to the photo, I think the painting fails to capture the subtle character messages that are apparent in the photograph. For example, you said you gave him this gift because he was so nice to you and your family. So, he's a really nice guy, right? I see that in his photograph. He looks like a gentle giant. But, the painting gives the impression of a cold, war-like 4 star general.
I think many of the other artists in the forum can give you better advice on technique than I can. My immediate observation would be to look at the drawing vs. the photo. Overlap them in Photoshop and compare the differences, down to the most subtle details. Second, I think the only major problem to work out is the looseness of the style...which is probably directly tied to your injuries. Being loose is so hard. My wife struggles with this too. Painting loosely is one of those things that looks much easier than it really is.
But please don't let this get you down. You did do a great job and I hope you're still perfecting your craft. You obviously have an eye for detail and concept.
Hope that helps,
John