Hello,

and thank you for any help you are kind enough to provide. I am adding hats and beanies to a little brand I have created. I am considering getting an affordable beginning embroidery machine in order to put our logo on beanies and caps. I am hoping you can share the realities of what is actually needed to do this, along with where i obtain them.
...an embroidery machine, hat loop? software to turn my design into a stitch able file for the machine? etc? I have no experience and don't know where to start.

Thank you again in advance,
Jon

Jon, my experience with hats is pretty limited, but if you're still waiting for an answer...
Not every machine could handle this and make sure to order the right loop. Better to ask your machine's dealer which one would be the best. When I decided to help my local club to make some capes, I ordered my Hoop-It-All from the shop where I purchased my machine because I had to make sure it would fit my machine. It wasn't cheap, but it works as a charm. 
If I am embroidering lettering I use a topping to lift the letters a little. And don't forget after attaching the hoop to your machine and get ready to start, to center the needle.