Which Camera/Which type of photographer am I?

Nice pocket camera or DSLR / shoot anywhere spontaneously or planned photo trips?

As Andy Ihnatko points out, the best camera is the one you'll actually use.

And that's the rub - which one would I actually use more? Obviously, I want both, but the question is which do I buy first? Right now I have a few year old ultra-zoom high-end point and shoot (12x zoom!!) - too big to fit in pocket, but not DSLR image quality or easy access to manual controls. Because of the so-so quality of this camera, I find myself using my 35mm more than I otherwise would simply because it feels more "real" and higher quality. I love shooting 35mm B&W, but I want to shoot more digital simply because of the greater flexibility and convenience - I already have more film shot than I can deal with in my limited darkroom time and I really ought to scan them all one of these days.

I am mostly a train photographer, and this is inherently something that you shoot on planned photo trips. But at the same time, I do want to expand my photography, and I have definitely missed many good shots in my daily life. Hell, I have some okay shots I managed to catch with my iPhone of a NECR train I happened to pass along Rt9 - the iPhone camera sucks but it's better than nothing. The real question here I suppose, is whether I'm more interested in advancing my planned railroad photography trips or my spontaneous non-train shooting, since that really determines which camera is more useful.

much more useful for planned photo trips
more expensive (though used, etc helps) - but a longer-term investment in the glass
lots of good used ones available
better potential image quality
feels more like 'real' photography
useless sitting on a shelf - will I actually go trainspotting enough to make the cost worthwhile?

Pocket Cam
already sort of have a pocket cam - the iPhone, it sucks, but it's there
more inconspicuous - always handy when dealing with Rent-a-cops
more versatile - it's not like it won't work just as well for photo trips even if it is a point-and-shoot
will I really cary it everywhere and actually use it??

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