"… I've never seen anyone consider friction due to preload"
I assume you're meaning friction between the bracket and the bolt head due to preload? As opposed to friction between the bracket and base due to preload, which is the basic foundation of bolted joint design...
"the ultimate state with a gapped flange, I'd have the reaction to F as shear on the bolt … things aren't going to come apart (or fail) until the fastener shears."
Disagree... Unless the bolt is quite far away from B relative to the height at which F is applied, the bolt will never see the shear because N will be quite large. If lengths are known, you can calculate N easily by summing moments around B. If µN is > F, there will be no slipping. Therefore the bolt will really never see shear. It will fail in tension by being "pried" apart. Of course, in this diagram the friction reaction is labeled as µN. Obviously µN is the maximum available friction force. In reality, the friction force value is simply F unless F > µN, in which case there will be slippage until the bolt contacts the edge of the hole.