Which camp do you fall into? Of course, this refers to fountain pens. If you have to clean ink out of your rollerball, ballpoint, or gel pen, it's probably because something very, very bad happened. But pen maintenance is an essential part of fountain pen ownership. You have to do it, and to the extent you can, you should learn to love it. Do I? Sort of.
Pen cleaning is one of those things people do either (1) all the time, such as, after they finish every fill of ink; (2) semi-regularly, such as whenever they change colors or every 1-2 months; or (3) whenever the pen clogs up and stops writing. I'm squarely in the second category. I don't find cleaning pens to be torture, per se (unless it's one of the rare occasions I've been using some sort of Noodler's permanent ink), but it's not something I necessarily look forward to.
I'll walk through the various categories of pens that I clean on a regular basis, from what I consider to be the least difficult to the extremely aggravating, and provide my perspective on which of the various filling systems are easiest to maintain. While the basic principle is the same for all--flush the pen with water--each system has its own peculiarities and quirks that need to be taken into account.
Syringe Fillers. Say what you will about Conid's Bulkfiller system being hard to get the hang of. Once you do, these pens are a snap to clean. It's like using a built-in bulb syringe (see below). Because the pen has such a large ink capacity, it's capable of pushing a large amount of water through the nib, reducing the number of times you have to flush it. If the pen's clogged, or if you've used an ink that's extremely difficult to clean out, you may have to disassemble the pen, but most syringe fillers have a small number of moving parts, and Conid even provides you with tools and instructions.
Cartridge/Converter. I have a growing appreciation for cartridge/converter pens because of how simple it is to clean and maintain them. While you technically don't need any special equipment, and can just use the converter to flush water through the feed and section several times, a bulb syringe and an ultrasonic cleaner allow you to thoroughly clean your pen quickly. For me, one of the best features of the cartridge/converter system is that you don't actually have to worry about cleaning the entire pen. Typically, the only part of the pen that touches any ink is the nib section and the converter (though I would recommend occasionally cleaning out the interior of the cap).
Eyedropper. Some people are going to be puzzled at this one. How, they might ask, is an eyedropper filling system--where the entire barrel holds ink--more convenient than the piston filler? Because there are no moving parts, and all you have to do is drop the entire pen into the ultrasonic cleaner. (In the "after" photo below, there is still some blue-black residue in the barrel, which I will clean out with a q-tip if I decide to change colors.) While disassembling a pen takes time, you don't have to do it that often! Eyedroppers hold a ton of ink, and if you use a low-maintenance ink and don't feel compelled to change colors, well, you can go a long time without cleaning that pen!