Hi Rich
After looking at this, I think it is the problem to which IamSam is referring yet without a step by step with images from you it is hard to know. And of course you provided step by step is pretty hard because it rarely happens to you. I could be totally off base yet I'm betting the issue could be operator error with a simple oversight. (Of course I could be totally wrong). The reason I say this is because I recreated what I think was the exact same problem and I was surprised too.
First, I just have a simple Layer with white for background and I created two paths (both are activated so you can see the path over the white area:
Then, I just selected the top path and click on the convert to selection button and I got a selection for the first path as in this image:
Then I activated the second lower path shown in the image below:
Now holding down the shift key I click on the convert to selection icon which should add them together yet it subtracts:
In fact, when I back out and look at the whole image, the entire image is selected except for the little triangle in the middle. Is this anything close that is happening to you and in checking the CC Draw mode it is in subtract mode:
Well, as it turns out. When I created this issue, the problem was that when I created the first path, it already was in subtract mode so have an inverse path (note the colors in the Path Panel shown in the images above. The second Path was also inverted. So when I created the first selection it was a "hole" and when I added the second selection (it was a hole too), I just filled in the hole more. So holding the Shift Key worked correctly. It was ll because I was working with inverted Paths.
There are a number of ways to leave the draw mode in subtract so I am suggesting that it was there to begin with just as IamSam suggested. Was easy enough for me to overlook so thought it was worth just putting out in steps to see what you think.
Let us know what you think
John Wheeler