Painter has or used to have an image hose as well and I think maybe Dogwaffle has something similar? I'm not sure how useful they are because, in addition to dropping randomly sized/positioned/rotated items it seems you'd also want the brush to be "smart" and not overlay the items, have them align in some fashion (along roads or something), etc. and I'm not sure either of those products can manage that bit.

Never messed with macros/scripting in Photoshop but is something possible using that?
M