Also, I'm planning on playing Wizardry I, and I've heard about its character import system. Do the levels carry over from Wizardry I - II - III, or do you always start over fresh?

Your levels do carry over to Wizardry 2. In fact, to get past the first floor of Wizardry 2, you absolutely must have a character with 7th level mage spells (i. e. a level 13+ mage); this is a hard requirement.

However, in Wizardry 3, your characters must pass the rite of passage to be usable; doing this reduces your level to 1 so that you have to start fresh. (In the Apple 2 versions, however, you can use the Wizardry 5 transfer routine to transfer the character back to Wizardry 1, use the Identify glitch to level up there, then transfer back to Wizardry 3; since you already underwent the rite of passage, you don't need to do it again.)

Wizardry 5 also puts imported characters back at level 1. However, unlike in 2 and 3, 5 lets you create new characters.

Wizardry 4 is very different from the rest of the series; so different, in fact, that transferring characters into or out of that game doesn't make sense.

For however much it helps, <span class="bold">you can upvote it on the wishlist here</span> (and <span class="bold">here</span>, and even <span class="bold">here</span>).

I must admit that my brother and I had wizardry 1 and 2 in the original box. We tried to to get it working recently on windows 7 and 10 and found that no matter what we did we could not get it to work.

We tried virtual xp machine, dosbox, and compatibility settings to name a few. It just does not like the new operating systems. Neither of us are programmers but we are both are older big time nerds with a history of making old games work on the computer.

My guess would be that is the one big reason we have not seen them on GOG yet, they just do not work.
:(

Are you sure you don't have the "booter" edition of Wiz1 and 2? I seem to recall (and according to Wikipedia it appears to be the case) that at least some copies of the PC editions of Wiz1-5 shipped as "booters" - i.e., that you were meant to boot up the game disk in lieu of a normal operating system (similar to how tools like Memtest86+ are used in modern times), and the game would start up automatically.

In this case, the game would essentially be a mini-OS, so running it under another OS is likely to be quite a pain (you'll probably have to use a full-fledged VM, but does VirtualBox, Xen, or Hyper-V support floppy image emulation this far down the line? I can't remember now).

If that is the case, try using the BOOT command on the disk image.
http://www.dosbox.com/wiki/BOOT

(Of course, you will need to get the image on your computer. It's easy on linux
(dd if=/dev/fd0 of=filename bs=512, but be careful not to mix up "if" and "of"), but windows will require a special tool to do this.)

(There might also be some copy protection to deal with, as well.)