Great list, just two recomendations: I totally recommend the Amphetamine app (https://itunes.apple.com/br/app/amphetamine/id937984704?mt=12) instead Caffeine app, it's much smarter.

And for gifs and screenshots annotation I rather go with Annotate app (https://itunes.apple.com/br/app/annotate-text-emoji-stickers/id994933038?mt=8).