Jul 10, 2018
This is a complicated, hobby, massive multi boot project, and I appreciate any help you can give. I'm not using VMs. If you don't want to read, that's fine. But if you like this sort of thing, please help me figure this out!

I am attempting to dual boot several operating systems on a new computer. I know how to do basic dual boots with windows, including older versions (3.1, 9x, 2k, xp) but only as dual boot.

This computer has Win 10 installed, and I'd like to not have to uninstall it if possible. I want these operating systems, probably in this order: (easiest install order, with the exception of Win 10, since it is already installed) Win 95, Win 98, Win 2k, Win XP, Ubuntu 18, Win 10.

Don't tell me I can't, (I know it's possible) and don't tell me not to (I'm going to). I have plenty of experience with virtual machines, but I don't want to do that. I want real, clean installs.

I know how to install each of the operating systems individually and I have all the install media (CDs and DVDs).

These are the problems I think will occur:
1. Win 95 and 98 require primary partitions, namely C:, which is currently Win 10. They will also destroy each other's boot stuff unless I use a boot loader.
2. Installing previous versions of Windows should(?) make current installation of Win 10 unbootable.
3. Possible issues with Ubuntu messing things up (haven't dual booted Ubuntu before, don't know. I've always done Ubuntu only installs)

So my questions are as follows:
1. I know I need a bootloader for Win 95 and 98 to run correctly (and not break each other) and probably to be able to boot into Ubuntu, (instead of using Windows boot options) but I know very little about boot loaders. What would be a good one to use, and how do I go about installing it?
2. Is there any way I can do this without uninstalling Win 10? Or at least bricking it so that I could use the recovery partition or a recovery installation disk to repair this installation? If not, it's not the end of the world.... I guess....

Here is my current Hard disk config. I am not going to get another hard disk, this all has to be on this one.

Efi partition | 161 GB Unalloc. (Will be all other OSs) | Windows 10 ( c: ) | Windows RE Tools | Recovery ( D: )

I have no clue why my recovery partition is available and visible in Windows 10, even in file explorer, but it is. Doesn't really matter though.

The space allocation will be something like this:
Win 95 (10 GB) | Win 98 (10 GB) | Win 2k (20 GB) | Win XP (80 GB) | Ubuntu 18 (30 GB)
The extra will be used for the boot loader and or other partitions for Ubuntu. I have heard that dual booting Ubuntu requires more partitions with specific purposes than installing Ubuntu fresh. I may also add a small Win 3.1 partition to make life hard for myself, or a file sharing partition available to all of the OSs.

I know this is a lot, but thank you to anyone willing to help. And, please, only tell me how one can do this, not how one can't or shouldn't.

Edit: I figured out how to post pictures. Here is my current config.

Also, I don't know where this should go, feel free to move it.
Jul 10, 2018
Question from crgbrntt : "Multi Boot bootloaders?"

What boot loader would be recommended for a multi boot system including multiple win 9x installations (that each need access to C: to be installed on) and an already installed win10? I know very little about bootloaders, so any recommendation or comparison of them that I can actually understand would be great!