Okay, so I used brew to update wine and downloaded the latest version of both PKHeX and .NET and got this error:
Failed to create CoreCLR, HRESULT: 0x80070005
0024:fixme:advapi:RegisterEventSourceW ((null),L".NET Runtime"): stub
0024:fixme:advapi:ReportEventW (00000000CAFE4242,0x0001,0x0000,0x000003ff,0000000000000000,0x0001,0x00000000,000000000019FDA0,0000000000000000): stub
0024:err:eventlog:ReportEventW L"Description: A .NET application failed.\n"
0024:err:eventlog:ReportEventW L"Application: PKHeX.exe\n"
0024:err:eventlog:ReportEventW L"Path: Z:\\Users\\j_wordington\\Downloads\\PKHeX.exe\n"
0024:err:eventlog:ReportEventW L"Message: Failed to create CoreCLR, HRESULT: 0x80070005\n"
0024:err:eventlog:ReportEventW L"\n"
0024:fixme:advapi:DeregisterEventSource (00000000CAFE4242) stub
So while an error is better than straight up freezing, this isn't much better. I've done some light research and it appears to be an issue with both PKHeX and .NET. Not much we can do about it