Question one can be solved with
six rotations of $R$-CWx2, $L$-CCW, $R$-CCW, $L$-CCWx2.
There's a GIF below in the detailed answer.
Question two can be solved with
fourteen rotations of $R$-CCW, $L$-CCW, $R$-CWx3, $L$-CCWx2, $R$-CCWx2, $L$-CW, $R$-CW, $L$-CWx2, $R$-CW.
There's a GIF below in the detailed answer.
Getting Started
First, let's assign a letter to each transformable sub-section of the grid; in this case I'll simply use $L$ and $R$ to represent the left and right sides respectively. Next, we begin by analyzing the letters available for plausible solutions. These are:
Question 1: Words won't fail.
Question 2: There is no exit.
Identified by @Morris' answer, and confirmed by the author in a comment.
Solving Question One
Solving question one is simple in that it only requires us to identify the fact that
the period must come after the "L" in fail.
In order to accomplish this, we must
ensure the period follows the L clockwise around the second grid.
To ensure this, we can
move the period to row 3 column 5 with the sequence $R$-CWx2.
This also
moves wor into a position that allows correct placement in the next steps.
Our next move needs to
put the L next to the period, in a way that both squares are moveable in $R$. We accomplish this with $L$-CCW.
Next, we need to
put the wor back where it belongs, which will also put the L. combination in its correct place. This is done with $R$-CCW.
Finally, we
rotate wor into its correct position with $L$-CCWx2 which subsequently solves the entire grid:
So the entire sequence for solving the first question is
$R$-CWx2, $L$-CCW, $R$-CCW, $L$-CCWx2; for a total of six rotations.
You can confirm my answer using an interactive version I made here.
Solving Question Two
This question must be solved by
focusing on the center column and being as efficient as possible with rotations.
To start,
move o into the center square with $R$-CCW then move it up next to the period with $L$-CCW.
The next step took a minute to figure out because
I originally tried chasing the phrase in reverse around the edges (e.g. r, e, ...); however, this was fruitless and maddening.
Ultimately, the next step is to
move the re combo away from the center and move the x back towards the bottom. I focused on the i squares for this since rotating the right square will move the x while moving the left will move the re; since i and i are interchangeable, it didn't matter if they swapped positions, so I moved the i in the right square to the bottom with $R$-CWx3.
Next, we
rotate $L$-CCWx2 then $R$-CCWx2 in order to place the x and prepare for our final rotations.
Afterwards, we need to
put the x back next to the e in the bottom row with $L$-CW.
This
aligns the ex we need for exit, so we rotate $R$-CW to move it into the center column, effectively preparing it for final placement while aligning the r with $L$-CWx2.
Finally,
we can wrap it all up with $R$-CW.
Which gives us a complete sequence of
fourteen rotations; $R$-CCW, $L$-CCW, $R$-CWx3, $L$-CCWx2, $R$-CCWx2, $L$-CW, $R$-CW, $L$-CWx2, $R$-CW
Just-in-case I fudged any of that, here's a GIF:
Feel free to use an interactive version I made here to verify this answer yourself.
Original Idea for Question Two
I originally thought of solving this
in the same manner that I would solve a Rubik's cube; however, I now believe this wouldn't be possible due to the interactions in the center column. However, I did successfully identify one algorithm which results in swapping the top two squares in the final column along with row 2 column 1 and row 3 column 3, while preserving the rest of the grid. The sequence for this is $L$-CCWx2, $R$-CCWx2, $L$-CCW, $R$-CCW, $L$-CW, $R$-CWx3, $L$-CWx2 for a total of 12 turns.
This algorithm swaps the following squares in the grid:
For clarity, this algorithm will swap $i$ with $i$ and $e$ with $o$ in the screenshot above.
Bonus Question
"Can you be sure?"
No; while most of the anagrams that I came up with for the text didn't much sense, they are still possible, and as such they cannot be ruled out without rigorous testing. Until all of the possible algorithms for the grid are known, I don't think we'll ever be sure on this one.
Furthermore, I feel that it's important to note that
with respect to the bonus question posed by the author, we cannot yet rule out the idea that the underscore represents a wild card character of our choosing. This is something I pursued, but due to my lack of sleep, it was not a fruitful adventure, though it was fun.