Multi-booting Windows 3.1, 95, 98, NT4 Workstation, win2000 Professional

I've read several FAQ's and MSDN articles on dual-booting, and have made a partial plan (described below).  Before starting, I'd appreciate some advice.  I want to multi-boot:

1. DOS (and then be able start Windows 3.1 using WIN).
2. Windows 95
3. Windows 98
4. Windows NT Workstation
5. Windows 2000 Professional

If possible, I don't want to use System Commander (which I have and like, but think the Microsoft Dual-Boot method should do the job).

My proposed partioning on a 10GB drive is:

2GB FAT16 to hold all five operating systems (in separate directories).  This partition will also hold a few Win31 applications and their data.  (If 2GB is not enough, I can drop Win95.)

2GB FAT16 partition to hold Win95 and Win98 appllications and data.  I assume it's necessary to install the applications twice, on top of each other so each OS can update its own registry.  But are there any problems with this "on top" approach?

6GB NTFS partition to hold WinNT and Win2000 appllications and data.  Again, I assume it's necessary to install the applications twice, on top of each other.  But are there any problems?

Must the OS's be installed in a certain order?  (I read something about Win95 overwriting boot.ini).

Will this approach work?

Is there a better way?
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Lee W, MVPConnect With a Mentor Technology and Business Process AdvisorCommented:
Your plan will ALMOST work.  Using Microsoft's boot management will allow you to boot to:

Windows 95 OR 98
Windows NT
Windows 2000

Windows 9x will allow you to boot back to a "Previous Version of DOS" - thus allowing you to boot to DOS 6.22/Windows 3.1.
Windows NT will detect 9x and allow you to boot back to it.
Windows 2000 will detect 9x and NT4 and allow you to boot back to those (note:  If you install NT4 to an NTFS partition and DON'T install SP4 or later, it will be inaccessible once you install Win2K as that will upgrade the NTFS system to NTFS5 which NT pre SP4 won't be able to handle.  I'd suggest installing NT 4 into a FAT partition.

As for dual booting Windows 95 and 98 here's the problem.  When 9x is installed it writes to the MSDOS.SYS the location of Windows 9x.  This is not switchable at boot.  So when you install 95, it's ready.  Then if you install 98, even if it's to a different directory, it overwrites the boot information and points at Win98 and now Win95 won't work at all.

HOWEVER, while I have never tried this personally, I think you can do the following:

Partition your drive into 5 drives:
C:\ = DOS/Windows 3.1x
D:\ = Windows 95
E:\ = Windows 98
F:\ = Windows NT
G:\ = Windows 2000

And install in that order.  In the end, your Win2K boot.ini should contain entries for the last three.  If you add the following lines, I BELIEVE you'll successfully use the NT/2000 boot loader to boot between the 5 operating systems.

C:\="DOS/Windows 3.x"
D:\="Windows 95"

You may also need to "SYS" the D:\ and E:\ drives using the operating system that is installed on those partitions
I would put each os's windir(dosdir) on a seperate partition.

As for the order I would go, dos (3.1) then 95, 98 NT and lastly 2000.

95 won't overwrite the boot.ini file but it will overwrite the master boot record so Nt won't boot but if you so it in the right order, it should be alright.
Adam LeinssSenior Desktop EngineerCommented:
Why all of the operating systems?  Depending on what functionality you need, you might be interested in VMware (  I can run DOS/Windows 3.1/Windows 95/Windows 98/Linux in Windows 2000 in a virtual box.  No separate partitioning needed.  It uses one file to emulate a whole partition.  Don't ask me how this is possible, it just is!  

Otherwise, it seems your plan sequence is fine.  Windows 9x likes to overwrite the MBR, and that why you want to install it before 2000.

Also, if you have System Commander, why not use it?  It's specifically made for purposes such as these.  You can setup your own autoexec.bat and config.sys files for each operating system.  I don't think NT's boot loader will let you do this as cleanly as SC will.
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elfieldAuthor Commented:
Thanks for the VMware suggestion.  It offers some interesting possibilities.

The software product I'm helping develop runs on many operating systems, and each has its quirks.  I prefer avoiding packages like System Commander (and perhaps VMware) because they introduce another level of complexity that may interfere with finding a particular problem.
elfieldAuthor Commented:
From the several comment, I think I have enough info to install the OS's.  Thanks to all.

But my plan also involves installing the applications "on top" of each other -- to save disk space.  For example, I need to run the Microsoft C compiler from the four 32-bit OS's.  Similarly, I'd like only one version of Netscape, Microsoft Office, etc. (again, just for the 32-bit OS's).

Will this work?  Or is it necessary to install separate copies for each OS (which I know will work, but consumes lots of disk space)?
Adam LeinssSenior Desktop EngineerCommented:
It depends.  Many applications install keys and other goodies into the registry.  For example, I use Office 2000. But a class I am taking uses Office 97.  So I installed it into my Windows 98 partition, which I never use (and I don't want to reboot to use a simple application).  So I just run it from Windows 2000.  When I do so, it comes up with several errors about missing links, but it still runs okay.
elfieldAuthor Commented:
My question is different.  I don't want to run, say Office 97, from Win 2000 after installing it for Win 98.  Rather, I want to install Office 97 for each OS, but always on the same drive in the same directory (on top of itself).  In theory, each OS has its own registry, and all should be ok.  A problem could arise if Netscape, for example, stored its preference files in a different format, depending on the OS. (I doubt that it does, but that's the kind of behavior that would torpedo this plan.)
As long as you re-install the applications into each o/s you shouldn't get a problem with the ms apps between the 32-bit o/s's but you may get a problem with 3.1.

As for netscape I am afraid I don't know, give it a go but in theory if the o/s needs a different file it should just install it, I'd have thought that if they have two files for two different o/s they would call them different names

elfieldAuthor Commented:
Thanks to all for the comments.  I'd like to spread the points around, but there seems no way to do that.
Try spreading them the same way you have to spread the o/s around your system.....boom boom tish

Never let it be said that engineers don't have a sense of humor ;)

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