As for Intimidation, I stopped using it after Morrowind as the NPC as disposition would plummet next time I talked to them. Does that happen in Skyrim?
Yes and no. There is no visible game mechanic that shows you your status to another character and maybe there is none. In most cases is one able to just restart the dialogue. So no. But there are a few dialogues, where the choice matters and it will change the relationship.
To be realistic, most people do not think in terms of numbers or have some sort of linear behaviour. The choice here is based on forgiveness and one just does not forgive an intimidation to 20% or to 98%. A logical/binary system is much better than a linear system to simulate social interaction.
A good, old example for this is: "she loves me, she loves me not, she loves me, she loves me not, she loves me, ..."
I have yet to see a "she loves me...0%...20%...40%..."