For me it's a complex question. There are many reasons why I am attracted to specific models. First, but perhaps not the most important, it will be a subject that is of historical interest to me. For example, I have this thing for F1 cars, drivers and history. I think the Williams F14B is one of the most innovative F1 cars designed, and created such a stir that the FIAA banned it, so I tracked down a 1:12 Tamiya kit so that I'd have sufficient detail in the build.
I am a US Navy veteran and spent considerable time in the Pacific. I was born during the great naval battles off Guadalcanal in 1942 and have intense interest in that place, period and the actions in the Pacific war in general. Having read "Shattered Sword" a couple of times, I want to build the IJN Akagi and have a model on order from HLJ.
Steve McQueen's movie "Le Mans" is one of my favorite, so I have a Fujimi Porsche 917 Le Mans car kit on the shelf.
Fascinated by the early days of flight, I have built a number of Eindeckers including one Wingnut Wings E-III kit which I reviewed for the IPMS USA website, and have the E-I and will get the E-IV. History here is the driving force for these kits.
I have read a fair number of books on the American Civil War and have a 1:96 scale Cottage Industry Models USS Monitor in progress, along with a USS Alligator submarine. I plan to build another ironclad or two as well.
As far as Wingnut Wings kits go, I'd say that I'm attracted firstly by those whose histories, or the histories of their pilots, I am familiar with. Then, I look at which markings I like. I tend to lean toward more wood than canvas, i.e., on Albatraii and Rolands. I am very grateful that Wingnut Wings produce larger two and multi-crewed aircraft because I knew little about them. I'd been concentrating on the single seaters but now I have built a Junkers, an F.2b and have a Roland, DFW, Gotha and Felixstowe...
But, I don't build aircraft that I don't like the looks of. This is, of course, entirely subjective and I accept that. I can get interested in an aircraft because of the way the kit is designed and the possibilities inherent in building it. The Wingnut Wings Snipe is an example. I know little of it's history, but the look of the aircraft is intriguing and the kit looks fun and challenging to build. The "Ninak" does nothing for me.
Funky aircraft are high on my list. I'm still kicking myself for not getting a Harry Tate. In that vein, I sincerely hope that Wingnut Wings goes a little more retro and gives us something like a Taube or a Spinne or Farman kit. That would approach the "too cool" line and I'd certainly get one of each.
Not much help for your poll I'm afraid.