So you have a good armor with Str +3 and Scoundrel +2 so you can use Scoundrel skills with him and one or two level you need to replace the armor, because it is now to weak. Therefore your warrior can't use his scoundrel skills again, because it is pretty unlikely to get the same combination again... If I want my tank to use some scoundrels, I would just teach him. Far more reliable.

Anyhow scoundrel is not really one of those aweful benefits for Str gear. It is very situational, but not that bad, because there are even Scoundrel skills which take Str in account, if I'm not mistaken.

What we are talking about is stuff like: Crossbow with + 2 Str, 2-handed weapon with +1 for dual wield and similar stuff.