I have no experience with the Craftsman model, but I have had a Drill Doctor 750 Classic since they came out over 25 years ago. It worked fine for the first 1,000 or so drill bits, but it takes some real finesse to do a goo job on the smaller sizes these days. I bought it back in the early 1990's when I was doing quite a bit of commercial work. At that time I was sharpening 50 or so bits per month.
I was originally doing them by hand, but it became so time consuming it cut into the time I needed to be making parts. Later I started sending them out, but being a small shop I was always at the bottom of the list. Sometimes it took several weeks to get a batch back. Then I bought a surplus Black Diamond sharpener from the place I worked. It was a great machine, but unfortunately someone else liked it more than I did. It was stolen only a few months after I purchased it.
Rather than going back to fiddling around hand sharpening the bits I purchased a Drill Doctor 750. I knew it wasn't a high quality machine, but I needed something quickly. As I said it worked fine for the first few years. As time went on the plastic housings started to wear and warp. After a while it was more time consuming to use the machine than it was to sharpen the bits by hand, so it went on the shelf.
Now that I'm retired and have a little more time I do use it on occasions. It took me and Jethro ( of the Beverly Hillbillies fame) some time and complicated cyphering to figure out the wear pattern and hence the proper way to position the bit to get it sharpened accurately. Through countless experiments and several sacrificial drill bits I have finally determined the proper methodology.
The proper sharpening procedure is as follows:
It can only be done during a full moon and after having consumed a minimum of 4 of adult beverages. Then you have to bow to the machine while standing on one foot and rotate counter clockwise, slowly reciting the chant OH-WA-TAFOO- LIAM. This has to be done a minimum of 6 times. Each time reciting the chant faster and louder. After the ceremonial introduction you have to insert the bit into the chuck, hold your tongue between the teeth on the left side of your mouth. Then tighten the chuck. Once the bit is firmly in the chuck you have to turn on the machine and insert it in the grinding port. As you rotate the chuck you have to simultaneously move your tongue from the left side of your mouth to the right. After sharpening every 3rd bit you must repeat the entire introductory sequence, including the imbibing the proper number of adult beverages.
The maximum number of bits I have been able to run through the machine in one evening has been 6. I couldn't tell whether or not they were sharp when I was finished, and quite frankly didn't care. However I was told the next day by the fellow hobbyists I was training to use the machine it was an interesting and educational experience.