I can't get DeedMapper to work with Codeweavers 19.0.1 under Mac OS 10.15.3. (It had been working with PlayOnMac under previous OS versions.) The app launches but returns a "PlotView.LocalPaint: Not implemented" error when trying to draw maps. I've tried the "Kitchen Sink" dependencies, to no avail. I've also tried simply copying the drive_v from PlayOnMac to Codeweavers, and still the problem persists. So I have to assume it’s an issue with wine32on64.
UPDATE: I have gotten DeedMapper to work by using the Kitchen Sink archive cited on https://www.codeweavers.com/support/wiki/mac/mactutorial/unsupported_deps. Out of the dozen permutations of dependencies I've tried, this is the only one that works. Prior to installation, I disabled the Mac OS Gatekeeper (sudo spctl --master-disable) because I found that fonts would not install otherwise. Note that this Bottle is Windows 7, not XP as ordinarily recommended for DeedMapper. Note also that the Kitchen Sink listed in the application database does NOT work.