I'm at a point where even if I get a bag for cheap I want to be happy with the condition and the quality of the leather. Otherwise I've wasted whatever amount of money it costI have some bags from 2008, 2009,with great leather. One from 2010 with horrible leather, and surprisingly a MAM from 2014(I think) with great leather. The Bailey I have is pretty new, the leather is thick but not soft at all, it's like cardboard almost. It will crease rather than slouch. Glad I got it for cheap on PM.
On the other hand, small flaws like minor corner wear or the inside not being totally spotless are more acceptable if you get a bag for cheap.