To your second question: if you could enable that, then your map would be running that entire expression for every feature loaded in the table, which would likely take a long time to run, might even crash your browser. Having the "show" link helps prevent this, and I don't anticipate that changing.
To the first question: in your screenshot, is the working popup coming from the same feature as you have highlighted in the table?
- Josh Carlson
Kendall County GIS