well you have your answer for the jpeg, as for digitizing what software are you using? If you do not have the correct software or are new to digitizing I would pay someone else to do it. there are a lot of very experienced people that can do it correctly and since this is for a paying customer that is way to go.
Think you ask how to digitize. To digitize you need software and lots of practice.
If I were you I would aks a professional digitizer to do this for you if you have not got the software,it would give a good job, much quicker and cheaper than buying software.To do a table cloth is lots of work. Make sure you ask enough money for doing this.
If you have a photo of the logo, scan it, so that you get a jpeg of it and then digitise in the usual way.
As for he price, don't ask me I always price far too cheap, hardly covering my materials. But you should take in account time spent, cost of material, running cost of your machine, etc.