You can easily check if the screwhole is vertical by screwing the screw underneath a couple of turns and eyeing it up. In a tool like yours with a positive insert, the insert is horizontal and the screw is offset slightly so that the insert is pulled tightly into the machined recess when the screw is tightened. Your idea of producing a recess on the other side of the holder has merit, and only the difficulty of small scale precision milling is against it. Most of the common positive inserts have sides sloping 7 degrees and the pocket in the holder has sides to match, that is difficult to reproduce.
Looking at your photos, I see a problem, there will not be much thickness left with such a small tool if there are pockets on either side.
I have machined loads of indexable tools to get them all the same height and can say with certainty that Sandvik, Kennametal, Seco, Korloy, WNT, Mitsubishi, APT, Iscar, Walter and the cheap Chinese ones are equally hard. Not so hard that they cannot be filed or cut with a hacksaw, but carbide tooling is the best way to machine them.
The Chinese toolholders readily available are so cheap, that unless you want to modify your existing one as an exercise, then simply buying a left hand one is best.
Edited By old mart on 04/09/2020 17:56:41