The rule of thumb is generally that for Windows games pre-2008ish, Parallels is a better choice, since they tend to rely on weird corners of Windows compatibility and 32-bit performance in Wine is still not always great. DXVK + MoltenVK is generally the best choice for anything post-2000s, pre-DX11, and GPT/D3DM is generally the best choice for anything DX11/DX12.
The rule of thumb is generally that for Windows games pre-2008ish, Parallels is a better choice, since they tend to rely on weird corners of Windows compatibility and 32-bit performance in Wine is still not always great. DXVK + MoltenVK is generally the best choice for anything post-2000s, pre-DX11, and GPT/D3DM is generally the best choice for anything DX11/DX12.