Mike,
I use Mint v. 19.3. I have used Mint since v 13. During this period Wine has gone from v.2.x to 6.x. Initially I used DesignCAD v2000, a Win32 bit program, which worked quite well but not perfectly. DesignCAD 17.2 would not work at all under Wine 2.x These days I use DC17.2 under whatever the latest version is of Wine and apart from the odd little quibble mainly to do with on-screen labelling, it works quite well. To be fair, DC17.2 is now quite old, ie about 2006/07 but it does all that I want.
FWIW, I have also used Paint Shop Pro v. 7 via Wine under Linux Mint with no problems, although I now use The Gimp. I have also resurrected Lotus Smartsuite under Wine. The only reason for using PSP & Smartsuite is because I still have old stuff saved under their proprietary formats which I can't open any other way, so what I do now is that when I come across an old file, I open it and then immediately save it under something more modern that I can then open using The Gimp or Libre Office as appropriate.
I have used Oracle's VirtualBox to firstly load Windows XP, and then via XP to load a DOS based database program which at the time I could not get to run under Linux in any other way. It was rather messy, and when, with some help, I got the database running via DOSEmu, I immediately dropped Virtual Box. Like Tomfilery, I too could save my data in a shared directory.
Although as I say, I am using old programs, and have no desire to update them, Wine has improved tremendously since v.2.x and I would suggest that it may well be possible to run a lot more Win32 bit programs under Linux.
Peter G. Shaw