Hi Scott,
I’ll give this a go…
When an ex-con returns home to find his estranged daughter depressed by an ugly world, he aims to make the entire town litter-free in an attempt to win her back.
INTENTION: must make the entire town litter-free (?).
OBSTACLE: ?
When he returns home to find his estranged daughter living in a squalid town, an ex-con, trying to start fresh, aims to clean up the place, in order to win her back.
- The problem here is “aims”. It should be a “must” - as if he has no choice. Usually if it’s “aims” or “attempts” - the protagonist at any point could easily give up and go home. We like it when our protagonist’s are in it to win it.
How about…
Upon finding out his estranged daughter is trapped in a squalid small town, an ex-con, trying to start fresh, must clean up the place, in an effort to win her back.
- “Trapped” might be too much. Perhaps “festering”?
Hmm. Could go deeper.
Upon finding out his estranged pregnant daughter is festering in a squalid, drug-filled town, an ex-con, desperate to start fresh, must clean up the place, in an effort to save her from herself.
(This one sounds quite gritty and intense. Admittedly - not sure if "desperate to start fresh" is necessary to the logline.)
Anyways - good luck with this.
Hope this helps.