Can you go down two rabbit holes at the same time?

Yes, but you can only do justice to one of them.

-or-

No. There is, in fact, only one hyper-hyper-dimensional rabbit hole in the multiverse. It intersects all possible problem spaces one or more times; any rabbit hole you encounter is just a sub-dimensional projection. This is why following one long enough invaribly leads to an entirely different problem space.

Assume that n issues are connected at some level, then deep-dive enough to find where they diverge. Instant multiple (semi-connected) tasks!