How to split string across new lines and keep blank lines?

I’d recommend using lines instead of split for this task. lines will retain the trailing line-break, which allows you to see the desired empty-line. Use chomp to clean up:

"aaaa\nbbbb\n\n".lines.map(&:chomp)
[
    [0] "aaaa",
    [1] "bbbb",
    [2] ""
]

Other, more convoluted, ways of getting there are:

"aaaa\nbbbb\n\n".split(/(\n)/).each_slice(2).map{ |ary| ary.join.chomp }
[
    [0] "aaaa",
    [1] "bbbb",
    [2] ""
]

It’s taking advantage of using a capture-group in split, which returns the split text with the intervening text being split upon. each_slice then groups the elements into two-element sub-arrays. map gets each two-element sub-array, does the join followed by the chomp.

Or:

"aaaa\nbbbb\n\n".split(/(\n)/).delete_if{ |e| e == "\n" }
[
    [0] "aaaa",
    [1] "bbbb",
    [2] ""
]

Here’s what split is returning:

"aaaa\nbbbb\n\n".split(/(\n)/)
[
    [0] "aaaa",
    [1] "\n",
    [2] "bbbb",
    [3] "\n",
    [4] "",
    [5] "\n"
]

We don’t see that used very often, but it can be useful.