At one point in time I had Win98, Win2000, Redhat 8, FreeBSD 4.6, and QNX installed on the same 20GB drive at the same time in a testing box.
My recommendation: figure out /write down your partition scheme first.
I'd install windows (98, then 2k) first. At this point you need to make the decision, do you want a Linux bootloader to boot the machine, or Windows. Either way works.
Install your linux distro next.
When you encounter the part of the installation where it asks details about boot loaders, this is where your decision comes into play:
Using windows boot menu:
Install boot loader to your /boot partition (IIRC). You will need to make a boot disk to use this method.
After you do that and complete the installation, reboot using the boot floppy.
on the command line, type:
dd if=/dev/hda? of=/bootsect.lnx bs=512 count=1
Change the "?" to the number of your /boot partition.
This will create a file called bootsect.lnx (obviously). Copy this file to your root windows partition (copy to floppy or shared drive, then reboot into windows, and copy to proper location)
You'll then need to make entries into the Windows boot.ini file (STW for tips on this). After that, it should be ready to rock and roll--on reboot it should show the win2k boot menu (with the option you added), and then the linux boot loader (I recommend GRU😎.
Using linux boot menu: (my preferred method)
Note: this applies to GRUB. I haven't used LILO in a while, an there's plenty of info out there if you STW.
Install GRUB to the MBR. Edit /boot/grub/grub.conf and add the following:
title=Windows
root (hd0,?)
chainloader (hd0,?)+1
Change the "?" to the number of your windows partition, counting from zero.
Save the file and it should work.
Note: I believe since Redhat 8 or before, the installer automatically creates this if it detects a windows partition during installation.
BIG NOTE: YMMV. I make no claims that this is guaranteed to work on your box. I've gotten both of these methods to work on my systems tho. STW for better and more detailed HOWTOs.