Hi Mandy - an interesting free program which I use for tracing logos and the like is 'Inkscape' which you can obtain from http://www.filehippo.com
To trace something you select the image which can be jpg, bmp, gif, plus plenty of others, then go to [Paths], and choose [Trace Bitmap] option. There are a few options which can be selected from the dialogue box to help in improving the final trace. Inkscape will trace colour images as well as mono. The result can be saved in a number of formats including .eps which some cutting software prefers. My own developing website is http://www.PhoenixGraphix.co.uk In the gallery are a few jobs I have been involved in and some of those cuts are ones that I have developed. The trucks belonging to KTC, I photographed the logo on one of their other trucks using a digital camera, then used Inkscape to develop the logo/graphic. As for specific fonts, unless you have the time to compare an original with the thousands available, you are better off asking the customer what lettering they use.
A couple of other sites you may like to look at:
http://seeklogo.com logos
http://brandsoftheworld.com logos
http://abstractfonts.com fonts
Mal