Rixasha: As much as I like Linux and Wine, I would find it somewhat odd to put together a whole dedicated retro box and then not run the games natively on it.
Hi Rixasha. The thread has evolved a bit. I was considering building/buying a dedicated weak PC or laptop to run Windows games natively on. After suggestions steering toward programs I can run on existing setup (Macbook Pro) I am now entertaining the idea of using Wine, etc.
A retrobox would be pretty fun though. I still have an old case from the 90's that I could gut. The once white case now has that wonderful yellowish tint. I could even keep the 5.25 drive just for old time's sake!