Because they would actually need to install this font/software. They can easily switch fonts and assume that everybody has Century Gothic as it's already widely installed. The additional IT overhead probably don't justify the impact on savings.

Holy over-engineering Batman! How about simplifying that solution with image-based backup software. Macrium Free or if you have some bucks to spend Acronis is easier and a bit more polished.

Didn't the users notice the significant performance hit when wrapping their whole desktop in a VM?

I hired a technician recently BECAUSE of his many years of customer service/phone support experience. It shows that he's been able to put up with a lot, work hard on his communication and that he wants to move up. He's worked circles around my now ex-business partner and has been an awesome employee.

If you can prove solid work ethic, tangible knowledge and you interview well you should be a desirable candidate. So either these companies are underestimating the value of your previous experience, or they're not telling you the real reasons they're not hiring you.