Family Matter was not viewed as the best technical rapping ability by most people. I would say that song would be Euphoria. Also, Drake wasted half of the song on nikkas that don't matter because he didn't have enough to say about Kendrick. His inability to focus on the only person that mattered in this is a huge reason why people said his disses didn't hit as hard as Kendricks.
And Kendrick wasted the first half of Euphoria babbling about a bunch of nothing - the second half of the track was elite though and definitely has a case for the best display of technical rapping ability in the whole battle.
My point however remains - if the battle was won through rapping and Euphoria was the best display of rapping ability, why wasn’t the battle ended there and then? It’s because the public didn’t tap in to see a rap battle - they came to see a mud slinging contest and they know there’s a lot more mud to be thrown at Drake because he’s outside way more than Kendrick.
And Drake focussing on twenty targets or one is redundant - he would’ve lost even if he geared his whole strategy towards Kendrick. The battle was lost as soon as Like That was the number one song in the country for consecutive weeks - that song doesn’t go number one if it’s not a diss track aimed at Drake, featuring two of the most popular rappers of the moment and arguably the hottest producer. The track going number one put Drake on the back foot immediately because the public were already letting him know they were against him and the two options he has (ignore or engage) put him in a lose lose situation - can’t ignore the track when the number one song being blasted across radio and clubs across the country is a diss track towards you otherwise he’s accused of ducking the battle which rightly discredits his claim of being the biggest rapper in the game. If he engages though he will have to do something spectacular as public sentiment has already been shown to be heavily against him.
In hindsight the odds were always stacked against him and Kendrick used all the above to execute his strategy at a top tier level. The only thing Drake did wrong imo was that he did try to out rap Kendrick as that’s what he thought would be the determining factor in the battle - Kendrick ended up beating him however by using the strategy Drake used against Meek which is kind of poetic lol