Harrowed and TYWM

My Posse consists of one harrowed dude with 3 bullets. i take 1 casualty as the loser of a shootout round. I send my harrowed dude home. Since my harrowed dude was involved in taking casualties does that make him a casualty as referenced in TYWM and setting the bullet number at 3?

Yep! A harrowed dude going home booted is taking 1 casualty. Therefore, use the bullets on the dude to determine if TYWM works.