Boss V1 - "When you try to rap fast you fuck up your flow" is quite nice but you sandwiched it between two gay disses and finished it off with filler.
Byron V1 - Gay flip is decent, but you keep following it up to the point where it makes you look worse. Boring delivery diss is quite good. Major minus for rhyming 'self' with 'wealth' twice. Bad mic diss.
Boss V2 - Launch pad flip is decent, hypocritical flip is nice, microphone flip is pretty good. The voice diss was alright.
Byron V2 - Name diss is slightly amusing. Crash and burn flip is alright. Internal 'ize' lines are okay. Finisher is terribly awkward, you could have put this line earlier in the verse and thought of a better finisher.
This is closer than I thought it would be, but I'd give Boss the win mainly due to Byron's surprisingly poor rhyme scheme.