Thanks. I figured out the problem.
I have two different Chrome profiles (work & home) running at the same time. My flow needed to connect to an open "work" webpage, and I told PAD to attach to the page "by title", and manually populated the title to join to.
What I didn't realize was that it was never connected, and I gave up on Chrome and got it to work in Edge.
Now, smarter, I went back to Chrome and can see that PAD was only recognizing open pages on my "home" profile. When I opened the page under my "home" Chrome profile, I was able to actually select the page title from the dropdown, and achieve a connection and properly select page elements.
Three things I learned which might help somebody:
(1) PAD is seriously lacking in the user-friendly department. It should indicate (for web connections) that (a) selecting from the dropdown is required, and (b) whether or not connection has been achieved.
(2) PAD only seems to recognize one open Chrome profile, so if you have two open profiles and its not working, try the other one.
(3) When I tried to work on my second monitor, the highlighted page elements were out of sync with my mouse position. Working on the laptop monitor fixed the issue (might have been able to also solve it by making the second monitor primary.)