Hi Scott,

I’ll give this a go.

INTENTION: must make the entire town litter-free. (to win back sister).
OBSTACLE: ? what/who is standing in his way? What/who will make this hard?

To some extent, there’s a ticking clock here. How many days of freedom? A few?

Some notes/ideas:
– To “threaten” to disown him doesn’t seem intense enough. Couldn’t she just “disown” him? I mean that should help him get his act together.
– I got rid of “promises” and made it “he must” because “promises” feels like he could back out or has the option to back out. I dunno.
– “remaining days of freedom” is vague. Let’s give him a clear ticking clock. Let’s make it hard. Perhaps two or three days?

Attempt 1:
When his kid sister disowns him, a former gang member must make the entire town litter-free during his last two days of freedom, in order to win her back.

– I think this is the essence of it. Looking at it – why does cleaning up the town win her back? Why must he do it? Is she a neat-freak? Is it her dream to see the town clean again?
– I added “former”.

How about…

Attempt 2:
In order to win back his estranged kid sister, a former gang member must make the entire town litter-free, within his last two days of freedom, (or else?).

– In this one I changed up the inciting incident.
– Can we make this harder? Push down on the obstacle? (Of course – cleaning up an entire town is hard but curious to see if we could make it harder for him.)
– Some ideas for obstacles? Perhaps his old crowd/cronies don’t want him to change and make it harder somehow?

– I suppose if he doesn’t do it – he loses his sister? But couldn’t he win her back in other ways? Why must he make the town litter-free?

TBH – neither of my attempts are great. Regardless, I hope my input helps in some way. The idea is interesting and I like how “cleaning up the entire town” is somewhat symbolic of his own “cleaning up his act/rebirth”.

Good luck!