I take it off before bathing. It's too much of a nuisance for me, to dry it.
I measure my progress by how faithful I pray the rosary everyday, and how active I am in avoiding venial sin as the possibility presents itself.
Pray the rosary everyday, avoid the occasions of sin, frequent the sacraments, and have faith in Providence.
Take it off, trust in God, and be at peace. Put it back on when you wake up.