When? Generally about 1 min after my mother hands me hers or a few moments after my sister leaves her laying around the house and I pick it up (mostly out of bordem).
Thus far I don't have my own and, honestly, I don't expect to buy one either. I find shifting from a DSLR to a compact camera hard now, most compacts are compact, small and light (which is great) but they lack controls and features I'm used to with the DSLR. I find the maze of auto modes never has the mode I want and I've no idea what the various modes are thinking or will give me. I also miss some of the creativity of having selective focus.
Lacking any form of manually controllable manual focus also hurts - electronic focus controls work only at the extreme ends - in the middle its nigh on impossible to get them to where you want.
Bridge cameras improve on a lot of those failings - offering some manual controls with regard to settings and often a similar shape (including mode dial) to a DSLR. However I likely won't be getting one of these either
To me the market has grown a little more and the keen DSLR shooter now has a new item out there that, whilst not cheap, is certainly suitable as the small camera. This is the mirrorless hybrid cameras - the Panasonic G series, Olympus PEN series as well as their new OM-D series. These offer small size cameras (the PEN series are almost identical to the small wallet cameras in body shape), but with high quality features. Giving you interchangeable lenses, manual focusing, slightly larger sensors than in most bridge or point and shoots (helps with quality and also improved selective focusing), a more pro build, more regular DSLR similar features and menu controls.
In short they are closer to mini-DSLRs than the bridge cameras, and yet with the micro4/3rds sensors capable still of the wide zoom range coverage even with smaller lenses.
In my view they are the ideal workhorse of the DSLR shooter wanting something smaller, but also capable and similar to what they are used to.
My dream - Olympus OM-D (called the E-M5 just to be confusing

) + flash + macro lens + something in the 200-300mm zoom range (which translates to something near 400-600mm in angles of view as compared to on 35mm sensors).