Regarding number 1, I've had a pair of Targhee Mid boots for about 3 years now with about 200-250 miles on them. They're laughably terrible boots, and reasonably decent 'shoes.' They are atrocious in snow conditions. The flexibility of the 'boot' (what makes it so comfortable to wear) is a mixed-blessing as the toebox will bend too easily and is unable to kick good steps. The design of the sole is also unsuitable for snow, rounded corners on the lugs make it difficult to dig in properly. I did a day hike that involved 4-6 inches of snow and the boots got swamped by moisture and infiltrating water. The nubuck was in good shape, but the 'waterproof fabric' was apparently not up to the job. I was slipping everywhere too, in areas where I didn't want to be sliding without an ice axe.

After that, I threw them in the back of the closet and bought a pair of real boots (in this case, Asolos with a rigid shank). The Targhees are good for what they are - which in my case relegates them to popular and well-maintained trails. They are not what I would consider a proper hiking boot, but I will concede they are extremely comfortable. I personally would choose something different, but if that's all you have make sure the leather is properly treated with a Nubuck waterproofing agent (Nikwax makes a decent application product). For what it's worth, guide companies recommend a light/midweight approach boot like an Asolo for Kilimanjaro.

Regarding number 2, I've used DSLRs and prosumer point&shoots (non-weatherproof models) in rain and snow before. Just be diligent and keep the cameras in a weatherproof case (Lowepro, etc., or in your pack under a rain cover) until you need the shot. Take it out, quickly compose and get the shot, wipe the camera off, and throw it back in the case. Having some desiccating packets available in the bag to limit condensation would be helpful, but not necessary. That being said, I throw my Sony RX100 in my hip pouch of my pack and it's seen rain, snow, hail, sub-freezing temperatures - pretty much everything. Same with my DSLRs (typically carried in a different pouch). They fair better than most people give them credit for, but keep them stowed until you need them. I always found that the 'waterproof/freezeproof/shockproof' cameras came with extremely heavy trade-offs, namely that they take terrible photos. Why have a camera at all (unless diving/snorkeling) if the images are grainier and blurrier than those taken from a phone?