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Wazzup! :D Here are some suggestions:

1). "My train stalled in the depot" - I think that Present Perfect suits here better, because this event has the impact on present time => "My train has stalled in the depot". But nowadays it's not so crucial anymore, so...
2). THE wind is blowing while waiting for me
3). I've got my woe from wit once again
Don't be sad, keep going with smile

In Russian, it definitely looks like he's talking to his woe from wit. So, it would be,
Oh, my woe from wit,
Don't be sad, keep going with A smile (don't forget "a")

4). With a silver, or being in need - the "a" is not needed, because silver is uncountable. If you need to put something there, so that it'd be singable, put "some":

With some silver, or being in need

5). Tell about those who are tired
I can't find the rule, but I'm quite sure that you have to say "tell someone" => Tell me

Tell me about those who are tired
Tell me of those who are tired

6). About the temple of broken hearts - would translate as И о храме разбитых сердец (without "из").
About the temple MADE of broken hearts

7). Star was shining nicely from sky => A star was shining nicely from THE sky
or
THE star was shining nicely from THE sky (in case it was some specific star:))
8 ). I woke up understanding - it's grief - it's A grief

Cheers! :D

Why, Alex! This is super! If need be my students will get your translation. There's no work for me left. But I'd suggest the following (I'm giving the same number of syllables not the break the rhythm.

1. With a shield, or maybe on it
With some silver, or being in need = May be in silver or may be in need
2. I woke up understanding - it's a grief..= I woke up to understand - it's disaster
(grief - страдание, неисчисляемое)
3. shining brightly - "nicely" is a misfit but I don't know why - just a feel.
Cheers! :love:

Please check out the alternative English translation I've just posted, that hopefully fully preserved the lead voice's rhythmic structure.

Well, after some careful polishing, I believe it does (as I always check my translations against music and lead vocals) :)