Beloved Oldooz, these are beautiful questions that you ask! I can see very well why these expressions are not easy to translate. How my admiration for translators has grown. Translators deserve medals!

Let's take first what is the easiest of your questions for me:

They are obstacles within you that you are making short work of. -- what does the "short work" mean?

Remember that the title of this Heavenletter #4457 is A Perfect Ripening Season. I think we can say that the theme of this Heavenletter is our haste in wanting enlightenment. The whole theme is why do we have to go through all we go through. Couldn't we just skip all this trial and turmoil?

Thus the title which seems to imply: Why can't fruit ripen overnight? Why do we have to wait?!! Expedite our trip. You could just bless us.

If God made short work of life for us, we could become self-realized in five years! or one year! Or instantly! Do we even need it at all?!!!

And so, if we made short work of it, we would hurry up the process, thus making short work of it all.

BUT WAIT, I see what you were picking up. You understand everything I said above! Oldooz, you found a typo!. This is my typo! And I did not see it, not even after you brought it to my attention. Thank you!

I will fix it right away! This is how that line was supposed to read:

They are obstacles within you that you aren't making short work of.

That's better!

The other expressions that you wanted clarified:

Why a whole lifetime or more to take for my shoe to fit? -- what does it mean "my shoe to fit"?

In this case, my shoe to fit implies: Getting enlightened.

Why make us humans have to go through this initiation at all? -- I cannot get a clear understanding of this sentence.

In this case, initiation refers to: Life on Earth

It hasn't always been easy, has it?

Thanks again, Oldooz!