Is he crazy? Has he lost his grasp on reality?
Maybe. That part might be debatable. But most likely he has a reason that might not be immediately apparent to you. Sitting as you do outside of his brain and unaware of his thoughts.
So let's examine for a moment some legitimate reasons for un-docking in a bad ship... on purpose.
As Bait
This might be the most popular reason of them all. A bait ship is often a sheep in wolves clothing, or a wolf in sheep's clothing, or some combination of animals wearing clothing. Whatever the analogy, it is intended to look like something it isn't. And more often than not, it has great potential to die a horrible meatshield death.
Down in Syndicate I used to use a ECM Drake as bait against these nasty Falcon supported gate campers. I once fitted all points on a Badger to try and catch someone. Fitting ships against type is a legitimate way to encourage combat. If you die in it, it might be hard to explain, but hopefully it worked well enough to counter that.
Sometimes it is important to have a truly great bait ship loaded with faction mods and expensive things. But other times, cheap and stupid win the day.
Trial
You can say what you want about fitting programs and they are extremely useful, informative and often essential - but they are not the same as beating your tank against a real enemy. More importantly however, learning to USE those mods in actual combat often requires actual combat. Sorry to break it to you, but this is known. Sometimes it helps to try something new out on an actual enemy ship. If you win, so much the better, but if you lose... well at least you know now.
Reading about combat is great and you should do that. But actually combatting out in space is even better. Real people are so unpredictable. They do crazy things like not fitting their ships properly too!!
( And yes, test server is a great tool for this if you have access to it.)
Purpose
My Sac fit got some attention this past week and many people pointed out that it was fitted improperly. Yes, yes it was. That's because it only had one very limited purpose - to explode ships undocking from a station. That was all it was ever used for. I have other ships in my hanger that are fitted for specific reasons and tasks. We all do, that's why we have ship classes! I have an Atron that has two warp scramblers on it! Why? To catch and kill Ventures, of course. That is all that fit is good for. Should it ever be killed by a Noob Merlin someone will say, "wtf?!"
Fitting ships for a single purpose is ok, don't let anyone ever tell you different.
Practice
Y'know the best way to learn to avoid enemy gate camps? Try to avoid enemy gate camps. This can result in the loss of a few ships before you get the hang of it. I got very good at avoiding bubbles in my stealth bomber back in the day, but I had to break a few eggs to make that omelet. That gets expensive if everyone of those test ships is fully fitted and carrying all the ammo types.
lolz
And finally we have the best reason of all - no damn good reason. I have a Venture fitted with guns that I am determined to someday kill someone with. That will probably end badly, but it will be fun. Fitting and flying ships for the lolz alone is a valid, distinguished and perfectly legit method of flying in Eve. As long as it is done in moderation, there is nothing wrong with it. We all get bored from time to time. Or just want to stop being so freakishly serious for a moment and lighten up.
I don't recommend flying a bad ship on purpose. Don't misunderstand this post. But there are legit reasons why doing so, even against your own better judgement, can be rewarding. Like anything you do badly, it only really matters when you get caught. Otherwise, who will ever know?