Most modern programming languages provide windows that Dr.Explain does an excellent job of capturing and identifying controls on. In my estimate, for 95% to 98% of commercial Windows applications out there, Dr.Explain is going to produce callouts that make sense and provide you with only a small amount of editing between the screen capture and a finished page.
For the sake of illustration, I sought out what I believed to be a worst-case scenario: programming languages such as Visual FoxPro produce screens that Dr.Explain is as yet unable to decipher. (The percentage of Visual FoxPro applications out there is relatively small, and growing smaller by the year since Microsoft stopped development of Visual FoxPro. So you may never have to document an actual Visual FoxPro application.) The below is such an example. I say "Visual FoxPro is probably an example of a worst-case scenario" because it has its controls "encased" inside a single window (I won't use the technical term for it here), which eludes Microsoft Spy++ as well as Dr.Explain to identify visible controls. The good news here is that Dr.Explain STILL enables you to deal with this situation easily: simply capture the whole window, enter the "Screen Editor" mode for the captured picture, crop your picture to just what you want to show (in this case, I wanted to keep the whole window so I skipped this step), and then in the "Designer" mode, click the New Control button in the tool-bar for each callout you want to create.
Voila! And it's STILL fast! This is yet another Very Well Done to the Dr.Explain team.
Initially the screenshot of this Visual FoxPro application only had one callout called "Client Area" which marked everything below the title bar. This is actually not Dr.Explain's fault, because Visual FoxPro "hides" its controls from "the outside world" for no particular reason except that the Visual FoxPro team had their own particular (unusual) approach for creating controls in Windows applications.
Despite this apparent "hurdle", as an experiment, I created 14 callouts for the screenshot below, and it took me only 10 minutes, minus the detailed descriptions of each callout. I also "shrunk" the overall screenshot image (to 70% original size) to help it fit inside HTML Help page more easily. Note that this size reduction can be reverted at any point later since the original image is kept intact in the project -- a very nice feature I think. I also "shrunk" the display of the Task List control (callout 1, to 90% of original size) for the same reason. All the other controls I left at their original sizes.
Time cost: 11 minutes (note this included entering names but not descriptions for each callout). This is somewhere close to 8X to 10X faster than if I had produced the below from a screenshot with my favorite graphics program!