The shield with hammer & orle is quite nice!
As to the crest, how about a demi-bear as in the arms? (i.e. with hammer & spike)—nothing really wrong with just the bear’s paw, but if the crest is sometimes used alone (e.g. as a badge) the half-bear will be more distinctive & more readily recognized vs a paw which visually could be a lion’s paw.
Also, not knowing Mr. Wilson’s family origin, use of the demi-bear would also allow the artist to use the occasional German style of omitting the wreath and having the bear’s skin flow into & form the mantling—though it would likely be a simpler style of mantling than your illustration.
Just thoughts for your, and his, consideration…
Originally I had a demi-bear, which I have since decided to go back to after talking to my fiance. She said that she liked the demi-bear better than the paw and that he probably would as well.
Snyder;95607 wrote:
http://i18.photobucket.com/albums/b146/Snydercrew/wilsion5_Wilson.jpg
A bear within an orle? Excellent idea 
I think the design is now excellent.
The one reservation with the emblazonment that I feel obliged to express is that it is not customary to display service medals (as opposed to personal decorations) with a coat of arms.
This is a much debated and sometimes emotional topic, but you should at least take a look at the AHS Guidelines on the website and perhaps do a search through the forum archives for various discussion of the issue, most recently http://www.americanheraldry.org/forums/showthread.php?t=6171.
Jeffrey Boyd Garrison;95608 wrote:
I like the orle a lot! :D
+1
Michael F. McCartney;95624 wrote:
As to the crest, how about a demi-bear as in the arms? (i.e. with hammer & spike)—nothing really wrong with just the bear’s paw, but if the crest is sometimes used alone (e.g. as a badge) the half-bear will be more distinctive & more readily recognized vs a paw which visually could be a lion’s paw.
+1
Crest: Out of a wreath of the colors a demi-bear Sable, holding in dexter paw a railroad spike Argent supporting over the sinister shoulder a Spike Hammer Proper.
Joseph McMillan;95634 wrote:
I think the design is now excellent.
The one reservation with the emblazonment that I feel obliged to express is that it is not customary to display service medals (as opposed to personal decorations) with a coat of arms.
This is a much debated and sometimes emotional topic, but you should at least take a look at the AHS Guidelines on the website and perhaps do a search through the forum archives for various discussion of the issue, most recently http://www.americanheraldry.org/forums/showthread.php?t=6171.
I agree with Joe, this is a very important topic for American heraldists to be knowledgeable about.
(incidentally, my personal preference is to follow the AHS guidelines on this in my own arms by leaving off service medals (non-decorations) in any public display which in this case is just message forums).
I was working under the guideline of:
2.2.3.1. Military and civil decorations awarded by the United States government or one of the states may be displayed as part of an armorial achievement as follows:
But overlooked the notice in 2.2.3.8, which settles the debate.
I can see the logic behind it, especially with "blanket" awards that essentially give everyone who serves a medal. But this is the wrong thread for this debate, so I will throw my two cents into the mix the next time it rolls around. 
Not everyone agrees with this particular limitation—me for one—but it has been the group’s consensus
