Privateer 2 was the only game I ever paid $100 for. It was worth it.
I recently finished it again on WIndows 7 x64 for the first time since Win98 days.
Both the DOS and Windows versions work. For me the windows version plays much smoother but the DOS version is slightly more stable.
If anyone is interested, these are the steps I took to play both the DOS and WINDOWS versions. All credit goes to others.
1. You need the original installation media for the DOS version. My copy was the deluxe edition which I guess contained installers for both DOS and windows. I don't think I still have them anyway but even if I did it's quicker to download them so I downloaded the ISO's for the DOS only version from a torrent.
2. Install Daemon Tools
3. Mount CD1 in your Virtual drive (mines F: for fakecd)
4. Install the latest version of DOSBox (0.74).
5. Modify C:\Users\<username>\AppData\Local\DOSBox\dosbox-0.74.conf.
There's 1 setting that's absolutely required to run the DOS version...
cycles=45000 Your mileage may vary with different settings, I tried up to 90000 which should be equivalent to a P75 or P90 but it ran too fast. Combat is playable with 45000 but planets slow the game right down, this is the reason I looked further into the Windows version.
Some of the settings I used are below but really they're all your preference. You don't need any of this if you plan to exclusively play the windows version.
fullresolution=1280x960
windowresolution=1280x960
output=overlay (or openglnb or ddraw)
aspect=true
scaler=supereagle
core=auto
cputype=auto
cycles=45000
[autoexec]
mount D D:\
mount F F:\
D:
CD Games
6. Run DOSBox and install the DOS version to a folder of your choice. If you plan on having the DOS and WIndows versions in the same installation folder then the DOSBox folder path must match the actual Windows path exactly. Otherwise you can make a copy of the DOS version later and put the windows files in it and copy your saves between them. For this though lets just say you install P2 into D:\Games\DARK which exactly matches the folder D:\Games\DARK in windows.
7. During installation select SB16 for sound and music in the installation and your controller type. I just used mouse so haven't tested joystick/throttle sorry.
8. Google and download p2patch.exe. This is the 1.17e patch and has a filesize of 572,482 bytes. Put the p2patch in your DARK folder and run it in DOSBox. It can be found here:
http://www.wcnews.com/webmirrors/tech/download.html 9. Download the awesome priv2windowspatch.zip with a file size of 1,821,940 bytes from the following page.
http://originalthp.solsector.net/privateer2win95/
10. If your DARK directory in DOSBox is the same as in windows, copy the following files from priv2windowspatch.zip straight into your DARK directory...
DARK.B50
DARK.EXE (rename to DARKWIN.EXE so you can run both versions side by side)
DARK.M50
dsetup.dll
dsetup16.dll
dsetup32.dll
GAMEFLOW.IFF
INSTALL.IFF
leak.dmp
PRIV2.KEY
PRIV2.PTC
READ.ME
WAIL32.DLL
11. If you want the DOS and WIndows versions in separate folders, make a copy of your DOS installation, copy the windows files to the copy and edit the path in DARK.CFG.
12. You should now be able to play the Windows version of Privateer 2. Do not enable any compatibility options.
13. At some stage you'll reach a mission that crashes and doesn't let you continue. Just load up the DOS version in DOSBox, complete the mission then switch back to WIndows.
Some other notes:
You may want to disable all anti aliasing other graphics options in your graphics card drivers so it doesn't corrupt the interlaced videos.
You may want to disable mouse acceleration (Enhance Pointer Precision) in windows mouse properties because it screws with DOSBox games (makes Privateer 1 unplayable for me).