https://bugs.winehq.org/show_bug.cgi?id=55513
--- Comment #6 from Jeff Smith whydoubt@gmail.com --- I reproduced the problem (with all builtin components). I collected and reviewed logs and ran some tests on Windows based on those. All of this led me to think it is not an issue with gdiplus or with icon/cursor loading.
Then I managed to get Paint.NET 3.5.11 installed along-side native .NET (3.5 SP1). This combination does not appear to have stability issues. I'm leaning toward this being a mono issue.