Rich, you got a lot of damn listening to do.
Epic Hangman coming!
I would dread having to do 24 writeups.
Well, his in older ones seem more the size of yours, Tomi's, and Luke's, but if they were the size of my earlier ones or Crow's in older roulettes...
Nah I've never written that much, that's just not how my brain works. I've always been more - but by no means entirely - on the "big picture" side of things (intuition, or "N", in Myers Briggs terms) than the detail side. I get the impression you lean somewhat the other way. For single-artist submissions, my write-ups are a paragraph, which may be long or short depending on how much I have to say. EPs and suchlike I'll always write a bit more.
Ariich is a freak, or somehow has more hours in the day than everyone else.

Sig'd.
But seriously, I just get a lot of time to listen to music during the week and in the evenings, almost all of which is while doing other things. Unless I'm in a meeting then I can almost always listen to music when working, when clearing/washing up in the evening, while commuting on those occasions I work in the office, etc. Getting 6-8 hours music in a round is no problem - on a quiet day I can listen through all of it in the one day. And for a lot of music I listen to, I have a good sense of my opinion of it after 2-3 listens (although I find it harder with single songs, which is exactly why I favour these up-to-20-minute roulettes), which is why my minimum commitment is 3 listens but for some of them will listen 4 or 5 times (or even more on occasion) if I'm unsure.
In terms of decent write-ups, yeah like I said I don't like to write loads of detail on lots of specifics, that's not really how I approach music anyway. I try my best to ensure I know what I feel about something, and then articulate that in a paragraph. It helps that writing concise assessments of things is literally a major part of my job.

Stupid questions part 1!
Do we submit round 1 and wait for results before each round? 
Send your songs, wait for your score, then pick your next songs depending on how much Ariich hated the last batch. 
I mean, you'd have to work pretty hard to send me something I hate. The lowest scores I've ever given have been 6.0/10, which just about scrapes through as "decent", and that was in my album roulettes where scores were on average slightly lower because people weren't picking out the best songs. One of those I probably could have gone slightly lower, but I was rounding to the nearest half back then, and it was a post-roulette submission anyway.