Is there any rule about splitting phrasal verbs?

Solution 1:

The informal rule is a stylistic one. Keep the complement as close as possible.

That really helps me out.

Clearly this is not a lot of separation, and to phrase it "helps out me" would sound awkward and awful.

That really helps out the children who are starving every day in Africa.

To put "out" at the end would simply require the reader or listener to wait too long to parse your verb as a phrasal verb.

To sum it all up: it's a judgment call.

To sum up everything I have stated in this response: it's still a judgment call.

Solution 2:

This from the 'Longman Student Grammar of Spoken and Written English’:

Transitive phrasal verbs allow particle movement . . . When the object of a transitive phrasal verb is a pronoun, the adverbial particle is almost always after the object.

It follows that both your examples are possible. However, if you replace a broke college student with the pronoun him, only That really helps him out is possible.

(Different considerations apply with prepositional verbs.)