For the latest wine versions, font-AA ("anti-aliasing", sub-pixel rendered font smoothing) works only for me for the wine version installed on the system, but not for the wine versions installed with POL.
Example: on my system I now have wine 1.1.33 installed. If I start my applications from POL, the font-AA only works when I select "system" for the wine version in POL's "Manage Wine versions" menu. If I install the same wine version 1.1.33 inside POL and chose "1.1.33", the font-AA no longer works. If I switch back to "system" it works again.
For the older wine versions, this was not a problem. For instance for 1.1.16, the font-AA works also for the wine version installed in POL. I tried installing "Enable anti-aliasing" feature, which is offered in the Install>Other category in POL 3.7.1. It did not work. Maybe, I should mention that I used my own registry edits to enable AA before POL had this functionality to turn on AA, using the following code: