When it comes to embroidering beanies, you have many styles of beanies at True to Size Apparel from which to work with, and the prices are shockingly low, especially considering the colors and styles of beanies available.
Any font will do for your customized beanie. Realize that beanies stretch and that there is no "front" or "back". The location of your custom embroidered logo should be high enough to allow the person wearing the knit beanies to fold it up a bit. Some embroidery buyers will order the logo to be positioned in such as way as to be visible on the fold once the lower portion of the beanie is folded up. That is my personal favorite method.
To avoid disappointment, take one beanie and your logo on a piece of paper and position it, the pin it, and then look at it on someone's head. Change the position frequently and take your time in this location decision of your logo embroidery. Give explicit instructions as to how far from the hem you want the logo to be embroidered on your beanie. Do realize that embroidery is not precise as to the number of inches to or from a point such as the crown, hem, etc. Your logo will be placed at approximately the distance from the hem, etc. as you ordered.
The cost of digitizing or setup is only $7.77 for a 5,000 or fewer stitch logo from the embroidery store at True to Size Apparel. Sewing of your logo is only $2.99 for the first 5,000 stitches - most logos are 5,000 or less stitches so that price is something you can hang your hat on.
True to Size Apparel does offer a free Embroidery Buyer's Guide, which is great if you are buying for yourself, your family or business. Guide is free and can be downloaded as a PDF file.