To answer your questions:
yes, it works, releasing too early is better than not releasing at all, and yes, you tend to overthink things a little grin

This Oscar dude is a pretty good singer and suits the song very well.
Good choice.
Also good choice of instruments minus the hihat in the intro, it sounds a bit cheap and MIDI-esque.
The chorus could be a little more dynamic (both in terms of volume and instrumentation) so that it stands out better from the verses.
But overall, the production is pretty good [Linked Image - Only viewable when logged in]
Enjoyed my listen!

PS: Get a faster computer to run Synth V in your DAW.
It's much more natural not to constantly switch back and forth between DAW and Synth V, and you don't have to constantly leave "the zone".