I know it's not sunshine week but here's something to maybe consider as a demoman if your team is headed into playoffs
Here's a clip of the rollout from the FACEIT cup, done by sigh: https://clips.twitch.tv/teamfortresstv/HelpfulHerringRaccAttack
Note: this only works on official sunshine. The first ramp that I surf up into top lobby is only present in the official version. Without this, this rollout is not possible at all.
I've also made a tutorial for anyone struggling to learn this, which can be found here and/or here
I'm also using a custom rollout script that I made for this so it's to be noted obviously that this isn't 100 percent ideal, especially if your first jump puts you out of the healing range of your medic, but I'm not going to worry about that.
Thoughts?