I can't give you the grammar behind it, but I can give you the translation and explanation. Hopefully there's someone who can answer the grammar part in more detail.
I guess I'd be fine with geting into a easy college and find a good husband/wife.
I think context is needed to explain this translation. Seeing the Japanese, the question I assume that is being asked is something to the effect of:
What are your plans for the future? (to a high school student)
So imagine a high school student thinking about this, not having a concrete plan yet, so he/she is throwing out a very vague and answer. The 「～ばいい」 here is not "should" but "it would be nice if" or "I would be fine with".
I read 「かな」 here as "I guess", something that is more vague than uncertain.
I can't tell you why, but the only way I would see 「かな」 as "I wonder" is if there was 「の」 before it, making it more of a question.
I wonder if I should enter an easy college and find a good husband/wife.