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You have to run the "disc" (the installer) trough the DOSBOX, and later run the installed game trough it, no compability modes should be needed.
I have win 7 64 bit and have done this with some other games, just read the info that DOSBOX supplies you with (use the "help" command or "intro mount" to find out)
I think it is Win Vista/7 that is causing this rather than 32/64 bit architecture.
I would recommend you to run the DOSBOX on the Macbook Pro (like I do, lol) since it is the only machine to ever have music working on some old DOS games when on my Windows machines music is not working (could be connected to some hardware/software that I have no idea about)
When comes to those first two parts (Arena and Daggerfall) you just install it from the discs and it comes with preset DOSBox-0.74.
I used to have it on both Win 7 and Win 8 on my old laptops and now have it on my brand new gaming PC (Win 10) and I can confirm it works just fine without any issues or other settings. I just double-clicked the icon in the folder called Arena (Full Screen).bat (possibly windowed) and it loads up but I used full screen on my 23" monitor and it works.
I hope it helps those who would like to get it on new PCs at 2019
Wow didnt realized this was still up.
I feel old now thanks! xD