"Put it in the hold" is a decent argument for point-to-point flights, or when you do gate checking. Otherwise it's a crap-shoot whether your stuff makes it (which can end a two-day business trip before it begins), what shape it will be in, and how long you'll have to wait. As soon as you have a connection, all bets are off.

How long you'll have to wait is mostly a function not of the airline, but of the arrival airport and the competence of the handling company.