I think “Spotting an opening…” needs a new para. The lipstick thing is a little over complicated, I think you could shorten it without losing anything.
The “pills like skittles” analogy doesn’t work for me.
“Small-to-medium-time” seems a cop-out, he’s a small-time crook, I think.
“Anticipated to sit..” should be “anticipated sitting”.
I’d take a look at condensing the first part of the story, it seems a bit over-written to me. The descriptions could be more succinct without losing the imagery – trust the reader.
Hope this helps, ignore at will, it’s only my opinion.