SPOILERS, as you might guess.
I just saw it last night. As I recall, he's retelling to Virg (my spelling, as he's "Virgil") the more significant ones and, he says, in random order.
He's so meticulous that I don't believe there's anything random to it. The family tale might even have been suggested by Virg saying Jack has a need for family ties, as his real ones were missing. That made me think he might've killed at least some of his family.
I suspect #1 (Thurman) was picked because she "forced" him to kill her. I think he was already in "the business," given his cruelty to animals in childhood, e.g. the ducky :( . He was headed somewhere else, maybe a planned murder, and this harridan bugged him so much he had to change his plans. That would annoy the hell out of him (pun intended).
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