I wonder, when he cries is it a mantra cry or an "I need you!" cry? Perhaps what's happening is that he's waking up and fussing and in your desperation for some sleep, you're intervening too soon? While I agree that it's good that he falls back to sleep quickly with your hand for reassurance, the end goal here is for him to not wake up at all.
What I would suggest is that you begin to introduce a calming phrase to replace your hand. Something simple that is always the same, "It's ok______. You're just going to sleep." Your aim is to have your voice to the place of your hand so use it every time. I would also suggest you stop bringing him into your bed in the morning because when you head back to work in a month, that is not going to work in terms of you getting up and dressed before he wakes.