Ok.. So I figured out the cause for this because I wanted to be able to do pathing as such; "api/{controller}/{action}.{ext}" so that I could use my media type formatter to use the same class and either return the data as json or in an xlsx (Excel) file.
I did some researching (although not enough I suppose) and the solution that appeared to work was updating my web config from;
<add name="ExtensionlessUrlHandler-Integrated-4.0" path="*." verb="*" type="System.Web.Handlers.TransferRequestHandler" preCondition="integratedMode,runtimeVersionv4.0" />
to
<add name="ExtensionlessUrlHandler-Integrated-4.0" path="*" verb="*" type="System.Web.Handlers.TransferRequestHandler" preCondition="integratedMode,runtimeVersionv4.0" />
Note the change in the path from *. to * which did allow me the pathing I desired. I at least didn't notice the missing images after I got this in place, or some were just cached.
Welp, I'm not sure why some files would work and others would not but, it did break "something". So I've opted to just K.I.S.S. and just go with the format "api/{controller}/{ext}/{action}"
Sorry for the posting but, hopefully someone else who follows the chain of events I went through can learn from my mistake.
This question is closed and the reason (IMHO) is PEBCAK.