Part of the upshot for Trump in appointing Heitkamp is that it basically clears the field for a Cramer Senate attempt, and Cramer was a very early Trump endorser, which would give Trump more influence in the GOP Senate caucus. I could see Trump therefore trying really hard to get Heitkamp to accept a position (it's Agriculture Secretary, I could see him giving her full latitude to do whatever she wants); she might reason that she could be a better advocate for her positions from within the administration than from a powerless Senate minority. Makes sense to me.
What I think is happening here (re: Heitkamp) is either:
a. She's serious about taking the position
or
b. Bannon and co. struck a deal with her that would entail Heitkamp being publicly considered for a cabinet position by Trump, which would give her bipartisan credibility in 2018, in exchange for her vote to confirm crucial cabinet positions.
Her vote's not needed for that. The Republicans have all the votes they need.
Depends on if they can keep their guys in line on some of the more controversial appointments. Sessions and Tillerson are certainly at risk of not being confirmed.
I don't think there's any particular opposition from within the Republican caucus to Sessions, and at least 1 Democrat has agreed to cross over and back him. Sessions will be fine. As for Tillerson, that might go over more poorly if the "neocon wing" decides they don't want to back him; they're numerous enough to tank any Trump Cabinet appointment they dislike.