It's never been a particular area of study for me, but in my drive by of the information, I don't think we know much about the level of contact. If there was, it seems there would have been sexual contact at some point, but from what I've read, there's no evidence of that. It's also possible that there was sex, but genetically they couldn't produce offspring, or if they did, the child was like a mule, incapable of reproduction, and no samples of DNA from the relatively small subset of offspring have been found. I've read about monkeys using "tools" such as sticks for weapons and leaves to scoop up water, but never of them deliberately assembling or making tools. The Neanderthal tools we've found tend to be somewhere between the monkeys and early humans, as they apparently shaped rocks for tools and such, but didn't go beyond that.
I've seen several reconstructions of neanderthal faces, and they go from being a human ape hybrid to being a face that cleaned up, would be unusual on the street, but not a "stop and stare" face.
With dinosaurs, there's what they were and what we fantasize them to be. I understand that the bird hip and cow hip dinosaurs are both extinct, but I have always contended that if crocodiles had died out before humans lived they would be referred to colloquially as dinosaurs. Various lizard hipped extinct species are referred to as dinosaurs, despite the fact that they don't fit into the strict "dinosaur" structure.
I see things as a continuum, and categories as being useful, but at some point arbitrary. You eventually have to pick a spot and say, "this is where it quits being one thing and starts being something else."
Monkeys do strip bark and leaves from small branches and stick them down anthills where the ants adhere to them. Then the monkeys eat them. Is that a manufactured tool? It is a modification of a natural object to be used to achieve some separate aim...