How hard to find a job? Depends who's looking for a job. People in top departments seem to find it pretty easy. People in bottom departments probably find it near impossible (talking about an imaginary ranking by prestige). I think Brian Leiter has good general advice as part of the Philosophy Gourmet Report (google it). One thing to know is that if you want to work as a prof you probably won't have much choice regarding the location. As far as I can tell, the reality is that most people are forced to move state/province or country to get a job. Aiming to get a job in a particular city is not realistic even for the very best candidate.

There isn't a whole lot of research funding in philosophy. Mostly people have jobs as profs and are allowed to spend some time doing research. In Australia and Canada, at least, I know that people apply for governent grants like in the sciences, and some get them, but there is much less money. These grants are typically used to provide short-term (1 or 3 year) postdoctoral positions to fresh PhDs (as well as funding trips and visitors). I'm under the impression that the majority of salaried philosophers work as profs, spend most of their time teaching, and never get grants. But that's just my personal impression.