Help with Multibooting Windows and Linux from USB

I've got a 32GB USB drive on my keychain (like, physical thing with car/house keys, not the Mac thing for managing passwords), and I want to make it so I can multiboot off of it... mainly for shits and giggles, really.

Multibooting might be the wrong word for what I want to achieve, I'm kinda out of my depth when it comes to "boot partitions" and "master boot records" and "boot information" etc.

Basically, the desired behaviour of this thing would look something like:

  1. Power on computer.
  2. POST.
  3. Presented with a menu to select an installation CD to boot from.
  4. Continues as if you had put in that CD in the optical disk drive.

(Of course, the USB would have to be set as the bootable device in the BIOS first).

So, a couple of questions regarding this:

Q0. Is this even possible? Short of writing my own bootloader, which, as exciting as that sounds, is also wayy beyond what I can do, it'd be nice if an already-existing one can be configured to do this for me.

Q1. Could this be done with GRUB? For example, put GRUB in the first partition of the drive, then, after the computer POSTs, select one of the CD images to boot from? Again, I'm way out of my depth on this, so sorry if I just gave anyone keyboard-induced head trauma.

Q2. If I understand correctly, each installation CD image would need to be in a separate partition on the drive? due to the differences in the way different OSes boot. For context, I've got two editions of Windows (7 & 10) and two flavours of Linux (Arch and Ubuntu) which I would put on there.

I guess this whole post boils down to: "How to put multiple bootable installation CDs on one USB drive?"

Thanks for any help!

Partitioning a flash drive just isn't very feasable, the best you'd do is YUMI I believe it's called

Hey thanks, I'll check that out.

But ya i don't think you can do windows with YUMI, you're best off with just a 2nd flash drive

Bugger. Oh well, I think I'll just carry a second one around and format it as necessary.

You can still store data on flash drives that have an OS on them just fine, they're just limited to FAT32 generally

While you can partition a flash drive to do just that, it's a lot of work and really not worth the hassle. I tend to do it myself using EaseUS Partition Master, but just so I can boot into Linux from the stick while having it appear like a perfectly normal stick whenever I insert it into a Windows machine.

For multiple installers, Initially I used a blank stick and one that had a bunch of .iso files on it. However that gets annoying real quick.
I ended up buying a bunch of cheap Kingston USB sticks and put labels on them. It's so much more convenient and the cost of the sticks can be justified if you think how long you'll be struggling to set up the multi boot one or preparing the one installer stick time and time again.

The pic is slightly outdated tho, I now have an all-in-one installer for Win7 and the Arch one actually has LMDE on it,

You need YUMI in your life

Yeah, I sorta figured that out most-of-the-way into writing the post, but I held out hope anyway in case anyone else had any ideas.

If I really needed them for like, a job as an IT professional or something, I probably would just do what you described; i.e put them all on separate drives. Mostly I just wanted to see if it was possible for the novelty of it.

Cheers for the insight!