I don't know how big is your pocket, but anything with non collapsible lens would struggle to fit in a pocket.
So I would agree with the and collapsible suggestions, as they would be perfect. And with your budget I think that will be easy.
Then again a FED2 from Fedka or oleg, with a Leica lens would be a good option to think about.
For someone with eyesight issues, a bessa T is an obvious choice. The RF window has a diopter, and the VFs are external. It also fits the price point; excellent used ones are around $300.
Wow, the response was better than I expected. I'll try to look up those cameras later since finals are next week. I guess a pocketable camera was a little unreasonable. I also tend to shoot wide around 28mm.
Are the Kiev cameras compatible with all Zeiss lenses and can Zorki and Kiev share the same lenses?
Yes the Kiev rangefinders can mount all contax rangefinder Zeiss lens, at least the pre war( certainly not the G series rangefinders), it's basically the same design as the contax II. As for the zorki they use Leica Screw mount lenses, maybe a wider choice of lenses if you really need a lot of them.
For me the Kiev/contax mount lens choice Is sufficient as I only shoot 35mm and 50mm. I can't say the Kiev viewfinder would be good for eyeglasses wearer, but I find it rather squinty but liveable.
I'd suggest a Canon P (with a 1:1 viewfinder) and the Canon Serenar 28mm 3.5 lens. Small lens, capable of great results. It needs a finder on the accessory shoe but when you take that off, the whole thing still is pocketable. It is in Leica specs so can take a Voigtlander 25mm, 21mm or even 15mm if you want to go really wide.
You can have both the P and the 28mm with the finder for under USD 600.
I wanted a Leica for quite a while until someone pointed out that the Canons I already owned stood up to and, in the opinion of many, surpassed the famous camera in function and build quality. These days I find my Canon III, Canon IIs2, Canon P(3), Canon 7, and Canon VI-T along with a Bessa R most of my needs are met with these M-39 cameras. A variety of lenses are to be had to fit most everyone's tastes. Good luck choosing Red