A military veteran eagerly tries to start the next chapter of his life but runs into Murphy’s Law at pretty much every turn, testing his resiliency.

Your version 2.0 is way clearer and is definitely giving me a better vision of your story.

The last clause (about the deceptive roommate) feels like it's a different beat to the rest, somehow. Maybe because a specific antagonist is included here, whereas the other challenges are less specific?

So maybe, as a suggestion, you can drill down to your protag's goal and then expand out from there:

A Vietnam vet fights to get his life in order while dealing with a corrupt welfare system and the deceptions of former friends.

Mine example's a bit lame, but hopefully you can see what I mean. With some brainstorming around what's most prominent in your story for you, you'll definitely get this thing in shape.

Thanks for sharing your updates -- love watching people brainstorm and re-work their concepts. Kudos.

Still vague, still using phrases that are a given in a story with conflict. What actually happens?

Full of commas. No need to mention true events at this point. Just give us an idea of the main narrative elements and the characters involved, while being specific and clear.

"A young veteran must adapt to life outside the army when a jealous college roommate tries to sabotage his career prospects."

I don't know if that's your story, but it is a story, at least the indication of one. A logline has to suggest the plot through mention of protagonist, antagonist, conflict, and stakes. All are present in the example quoted above. Give us something like that and you're set.

Version 2.0:

Mostly based on true events, a newly discharged veteran must use his resiliency when faced with challenges involving career hurdles, obstacles at college, and a deceptive roommate.