@Asyas_illos I like both of your ideas.
I didn't get the werewolf one at first, since there wasn't a bite mark that I could see, but the finished version would have made that clear, so I think it would come across easily then.
This angel pup one is really developing well.
You might want to consider adding a scythe blade to the baby-angel-of-death's staff, unless you want to stay further away from the Grim Reaper. (I had to look up the difference between sickle and scythe to make sure I got the right one!)
(These are all scythes. The sickle is the curved one that was on the old USSR / Russian Flag.)
Since you want him to be friendlier, you could also change the scythe to a shepherd's crook — or just stick with the current staff.
The edge of the waterfall is very straight. Are you doing that to emphasize the "end of the road" concept?
I agree with @AngelinaKizz that the recycle sign isn't the same as a written sign. And with @Chantal-Goetheer that you may not need it at all anymore. Either way, I think it works.