I look for a few things.
First, and foremost, ergonomics. I need a pen with an extra wide (11.5-14.5mm, ideally on the high end of that) section, but which at the same time is relatively light weight and well balanced. Oh man, that balance, that's important. I thought a Pelikan M1000 was going to hit the sweet spot, but nope, they're so ridiculously back heavy because of the excessive brass in the filling mechanism (I assume because of the bass ackwards idea that many folks seem to get that higher weight/mass=quality) that even that lovely springy nib can't appease me enough to tolerate it. I would just find it annoying if all things were normal, but I have a neurological condition that results in intense pain with pens I have to fight to write. Either a pen works well for me, and I can write for long sessions with no problem, or it doesn't, and - no middle ground alas. Other features matter too, like material. Metal sections, especially smooth... sorry, no. Just no. No. No. Nope. Omas, I love you, but what the hell? The new Paragon would be perfect, except for that damned metal section... why? Omas, why? Give me a pen the size of a new paragon, in Arco Bronze celluloid, with the section the same material as the body, and I would be throwing my money at you. Hell, even with regular cotton resin models.
Second, I want it to be beautiful to my eye. Which can be tricky. There is a fine line between pretty and tacky I generally err on the side of conservativeness. Flashy colors and lots of gold (I seriously don't get why I like arco bronze pens, but I do, which sort of contradicts this) tend to make me recoil a bit. Yet I see beauty in many very conservative black and gold designs. Beauty is in the eye of the beholder, and all.
It takes all of this to even make me consider throwing a lot of money at a pen nowadays. I'm really getting a feel for what I want now, so finally I am starting to look at the more expensive stuff. At present, what catches my eye strongest are big Urushi pens. From Nakaya 17mm Cigars and Dorsal fins (v1 and 2) to Danitrio Denshos and Mikados. Especially the Denshos and Mikados. I am equally torn between shu-dame, ki-dame and midori-dame Urushi variants - no flashy maki-e (not that I dislike it, my wallet just can't touch them). Soooo pretty. I'll probably be getting one within a couple months. Or at least ordering one. But I'm also looking at all the options for custom made pens (Hakase, Romillo, Newton, Scriptorium) to meet my wants.
Of course, I'm kind of looking at an expensive pen from a weird standpoint at the present. Because of my current condition I have had to retire way too young (44) and am looking at long term fixed income living, so my expensive pen dreams are going to be limited to one, maybe two based on store credit and "fun money" savings that I have now, and then they're going to have to last me as treasures for a LONG time, because I won't be buying anything nice well, pretty much ever again the way things are going. But I've accepted that. As I see it, it's nice to have a few treasures to enjoy, and pens can last a long time, even when used daily - I can hold them, feel them in hand, and use them. Objets d'art that live to be used, not just looked at. It helps further that writing really has a theraputic effect, helping me escape/shift my mind away from my physical problems when medicine can't.
Anyway, yeah - I've been asking myself the very same question OP, and those are the answers that come to my mind.
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