This is one of those questions that has many answers. It really is dependent upon the person who will be digitizing.
A really good digitizer will not come into their own until about 2 years of experience. Some, if very artistic and PC competent, may do better, but it is a lot of work.
A truly good program will cost at least $1,500 and up to - - $40,000.
If you really want to talk about digitizing and the programs that are available, I recommend that you make a list of why you want to do it AND be realistic about the time you have to invest in learning those programs. You may find it is a lot less frustrating to have your 'special' items digitized by a professional.
Pat, The Avid Embroiderer
If you are interested in selling your projects, you can determine your costs and profits quickly with my Spreadsheet.
If you want a lot of great information on working easier, faster and more confidently on your computer, check out my Tips and Tricks.
If you want to see my pashminas (that I successfully sell retail) check them out here. I also wholesale them.