Yes, I think you can "enter" while going away from uke. The timing is nifty and the window of opportunity is small, but it can happen. With slow, repetitive drills done properly, you can get the sensitivity and "feel" of the timing. Gradually speed up and it becomes an intuitive tool like any we practice.
If you enter and occupy a portion of the space uke needs to have good balance just before their posture is "firm", the uke must change their position and irimi has happened. While the uke is starting their recovery, tori uses the energy uke is creating to continue the kuzushi and fit to make a technique. So, yeah, I think ALL connections should be irimi.
The only other way you can connect (as I picture it...) is to take uke from a firm, balanced position and overwhelm their ability to stand up. This works at a certain level, but with well-trained budoka you will have the energy you just created used against you.
As usual, this is easier to feel than articulate.