So I have a telescope controller. It's a little remote thingy that connects to some servo motors and can move them to track stars & shit.

Here's a quick recap of today's insanity:

Thingy works, but software complains that the firmware is old.

Ok, no problem, I'll just update it. Found firware files and a shitty little Windows utility to flash them.

So how does the thing connect? Why of course, it's RS-232! What did you expect, USB? WiFi?? hah,lol...
Ok, not problem, I'm prepared for this - I bought a USB->RS-232 adapter some time ago - that should do it!

Firmware updater runs, starts uploading, gets to 3% and fails. Thingy is now bricked.
No problem! I'll just flash it again - the bootloader is intact. This time it gets to 4% before it fails again.
10 attempts later and never got past 4%. Tried different baud rates, serial settings, etc.

Helpful dude on web forum mentions that USB adapters tend to cause problems: Chinese clones, crappy drivers, the usual.
"Just connect it to your serial port directly!" "Wow, thanks, that solved it!" -- the forum thread is dated 2006.

But I have a serial port - on a Thinkpad 760E from 1996! I'll just connect it to that!
It doesn't boot. It used to - just 3 years ago I got it to run (win98) perfectly! But now it can't find the OS.

But I know there's an OS, I just need to fix the boot settings. Let's go into the BIOS setup by pressing F1!
*nothing happens*
The F1 key is broken!

Fuck it, let's just boot something else. Can it boot from a CD? Nah, too old. What can it boot from, then?
FLOPPY DISKS.
*I go to the fridge and grab a beer*

But guess what? I have some! A few years ago I went in search of them to play around with this exact laptop. And actually found a fresh, unopened pack of 10 floppy disks - in 2016!
And what's even more lucky? Back then, I actually still had a Q6600 system lying around that had IDE connections and so I scavenged a literal junkyard to find a floppy drive.
So what did I do with it? Did I get a copy of win95 and loaded it on my stack of flopies as a backup? Maybe Linux 2.6? OS/2 at least? Nope. I loaded only one single floppy - with the Plop boot manager.
*light facedesk*
But ok, that still helps! I can force-boot from the HDD, bypassing any BIOS trickery that would require me to...well..get into the BIOS. So I do that.

Success! Windows 98 appears! Yay! And then it disappears! Yay..oh, wait..no, that's bad. 
"HIMEM.SYS is missing". Fuck. Corrupted files? The disk is *really fucking old*... But hey, at least I have a backup HDD with another win98 install.
I swap the current 2.1GB disk with one with a whopping 1.4GB of capacity! 
"HIMEM.SYS is missing". Fuck.
HIMEM...that's extended memory, right? How much memory could this thing even have??
I open it up. 1 ram stick, 1 empty slot, 1 soldered ram chip. Fuck it, do we really need an extra 32MB of RAM? What are we, fancy? I take the stick out.

Success! Windows 98 appears! Yay! And then it disappears...have we been here before??
I almost yank the plug, but then...a login screen!! A few attempts at guessing an early 2000s passwords later, I'm in a win98 system. Finally!
Now what?

Yes, of course, I need to flash that thingy. Just run the little utility and...wait.. Where did I get it?
Right, the Internet. *carefully inspects all the ports on the machine* "no USB, I guess that makes sense, but that looks like an Ethernet port!"
*looks closer* It's RJ-11 with a little modem icon next to it. *sigh*

But there's an optical drive, right? I can use that. Just burn the files to a disc and put it in. Great, now I'm off to find an optical drive in 2021.

I find a laptop, or more specifically, half of one. No matter, who needs a laptop screen when you have a TV and a bucket with every video cable adapter imaginable?
Now I only need the media. A blank optical disc shouldn't be too hard to find, right? I guess, not, because it only takes me half an hour to track one down.
10 minutes of confusing because I haven't burned something onto a disc in 10 years later and I have myself a freshly-baked disc that will surely solve all my problems.

I put it in aaaaaand.....nothing. This CD drive is either broken or requires drivers - both of which mean, that I need to find another way of getting files onto the machine.

[the following section is shortened, because it ended up not working anyways]
Ok, fine, I give up. I'll use a floppy disc.
Could I, perhaps, use the serial port to share a folder? a few hours and two win98 VMs later, I had the answer: no. No I couldn't.
Luckily, I still have that floppy drive from 2016. Unluckily, it's not a fancy USB one.
I have only one computer left that is old enough to have a floppy drive port. The power supply seems to be dead.
I have another computer with a working PSU, so I hook it up to that one cables running between two cases - I don't have to unscrew shit!
But of course, that PSU is a custom OEM one from HP, purpose-built for a 2018-era business machine. That means no Molex connectors, let alone the small ones for floppy drives.
Soldering iron is on the other side of town, so making cables is out of the question. 
But what else has a molex connector? Why, an old USB 2.0 IDE adapter, of course. In the power it goes, and now the final system is powered from two separate power supplies, neither of which are inside its case.
And it's dead. The floppy drive is dead. Windows just pretends it's empty, but Linux actually gives a descriptive error message. The fucker is dead.
[this concludes half a day's worth of work that ended up being worthless]

Back to the closet of old tech it is, and this time, the stars are aligned. An HP business laptop from 2003! With not only a floppy drive, but USB and Ethernet as well!
Could I, perhaps, use the serial port to share a folder? a few hours and two win98 VMs later, I had the answer: no. No I couldn't.