Ideally the games should be freeware, a balanced length, and above all else FUN!  

Also quickly mention in the post if you would volunteer to lead the playthrough. Perks include getting access to a walkthrough as well as a comfortable chair. Spoiler alert: The comfortable chair is a myth. I don't personally feel like volunteering. 

My preferred choice would be for us to play Out Of Order by Hungry Software. Comedy, science fiction, hand-drawn artwork, electronic music, fluffy dog slippers. Sold on it yet? Trust me, you should be. Tim Furnish almost single-handedly made this game by himself over the course of three years. 

I don't think it needs to be a freeware game, I'd prefer to play with all you lovely people here through one of the many games I've bought that sit unplayed in the backlog!

If commercial games are on the table, then I heartily vote for The Council. Equal parts serious storyline with a cheesy tone (some of which is unintentional), it's easily my ideal combination. Best graphics I've seen in a game, second only to Kingdom Come: Deliverance.

Plus, it has some of the best 'quality of life' features, such as 'failing forward' so the game keeps going to the ending even if you massively mess up certain puzzles. It's split into episodic chapters (the whole game is a complete package, mind you) which will keep things bite-sized for a community playthrough.

https://www.gog.com/en/game/the_council

https://store.steampowered.com/app/287630/The_Council/

I'll suggest and lead The Blackwell Convergence. I like the idea of revisiting all the Blackwell games in CPTs.
To accomodate request for freeware, I'll suggest and lead King's Quest II remake and Clotilde Soffritti in: Never Double Park your Spaceship.
As for the backlog.. I could lead Kathy Rain 2? If anyone else wants to take the lead on that one, please do.

Just to clarify my position, the reason I mentioned freeware games was to avoid financial barriers for people participating.

However, I would much rather play The Council to be honest. Pacing issues were a small problem we experienced when playing IMAGinE together. This can be resolved with an episodic game coupled with 'failing forward' mechanics.

All good game suggestions so far, Bob.

I'll suggest and lead The Blackwell Convergence. I like the idea of revisiting all the Blackwell games in CPTs.
To accomodate request for freeware, I'll suggest and lead King's Quest II remake and Clotilde Soffritti in: Never Double Park your Spaceship.
As for the backlog.. I could lead Kathy Rain 2? If anyone else wants to take the lead on that one, please do.

Blackwell Unbound would be the next game in the series if we're going in order 
I'm happy to revisit the Blackwell games, but would suggest they remain broken up with at least a couple of other games in between them.

What is the backlog? I feel out of the loop. 

What is the backlog? I feel out of the loop. 

All the games I've bought over the years that still remain unplayed!

Yeah, I know that. But you didn't suggest any games nor added a link. Which is why I was out of the loop. Not because of the term itself.

Blackwell Unbound would be the next game in the series if we're going in order 
I'm happy to revisit the Blackwell games, but would suggest they remain broken up with at least a couple of other games in between them.

lol yeah good call! Let me fix my suggestions and include those by Legerdemancy.
I feel that, I'll keep suggesting Blackwell Unbound as one of the options and we'll see when its time is due. It's nice to see different aspects of the genre in subsequent CPTS.

NEW GAME CPT:
The Council - no leader yet. I think there will be a good audience for this one.
Kathy Rain 2: Soothsayerl leader BobVP (or anyone else up to the task).

THROWBACK:
Blackwell Unbound - leader BobVP

FREEWARE:
Out Of Order by Hungry Software no leader yet.
King's Quest II remake - leader BobVP
Clotilde Soffritti in: Never Double Park your Spaceship. leader BobVP

Just a summary, please keep adding suggestions, especially if you want to take the lead!