I think it's time for Mastered Roulette...expert is a joke.

[Velnora]

It doesn't have to be tomestones, I just put that in there since that falls in line with all the other roulettes.

I thought about adding a new currency that is used for trading for glamour, minions, housing items, or "Master" specific items at the Master Trader.
Or specific mount that only drops in Master Roulette, or a trans mog item that is tied to specific dungeon.
Housing items that are tied to master roulette to put on display.
Purchase highest tier materia with this currency also, to sell or use.
Special titles tied to Master Roulette.
Special achievements tied to Master Roulette

The whole idea is to make it optional, but not required. If it's not your thing...you don't have to. If you want to partake and achieve those goals...go for it.
Ultimate isn't required
Savage isn't required
Extreme isn't required
PVP isn't required
Housing isn't required
crafting isn't required
gathering isn't required
Gold Saucer isn't required
Roulettes isn't required

FFXIV is brilliant in what it describes as fun...it let's the player decide. I don't see the harm or problem in suggesting adding difficulty to the roulettes. Hard modes were great and added a fantastic spin on great dungeons.

Expert roulette is no longer expert...it's just another daily chore.

My current daily chore list (takes about 2-2 1/2 hours to complete):

Farm for map sell map
Check MB prices, farm for mats to make 250,000 gil for the day (personal goal)
Setup retainer 18 hour ventures
Setup Squadron 18 hour run
Idle banter in FC chat while I post items, setup retainers/squadrons
Run expert, 50/60/70/, trial in about an 45min-Hour (preferably with FC as it's faster, and I like helping them out)
Check Party Finder, might run an extreme or savage.
Check auctions once more
Log out.
Wait for FC weekly High End raid once a week

This works for my schedule and lifestyle, but I would LOVE to change party finder and expert, 50,60,70, trial for a "Master Roulette" since I just don't need tomestones at this point and I want the challenge. Hell I would probably play longer if those challenges existed.

Unreal was a test I felt...just to see who would want to go back to try old content at level 80. Maybe it's not something everyone does. But it shows that they CAN do it...and to me that's promising.

Nothing is required, yet there is a whole lot of content that gives zero incentive to run it. It's all a bunch of salad. No meat and potatoes.

[Payadopa]

How many failures on the boss that you see every day is still fun? How many times it's fun to wipe to that particular pack of mobs because bard keeps hitting sleeping monster with AoE or tank forgets to interrupt big spell? Because something tells that snapping point comes quicker than you think.

History shows that players rather not engage with the content or leave the game if daily grind gets too hard. It happened in WoW on the release of Cataclysm, it happened in XIV with shinryu, when good players would rather lower their ilvl than wipe with newbies 10 times in a row. And same will happen with hard roulette.

I still do old content for fun and no real rewards (and many PUGs) so I don't know what to tell you. And nobody is forcing you to do every roulette anyway.

[Shurrikhan]

History shows that players rather not engage with the content or leave the game if daily grind gets too hard. It happened in WoW on the release of Cataclysm, it happened in XIV with shinryu, when good players would rather lower their ilvl than wipe with newbies 10 times in a row. And same will happen with hard roulette.

You're comparing apples to oranges here; you might as well complain about people not wanting to run Eden Savage with players who don't yet even understand their jobs. Heck, that'd actually be more apt an analogy to the Unreal roulette proposed, but also no less avoidable an issue than those the roulette would face.

The roulette necessarily would not include players struggling to get through MSQ content for the first time; they'd have to have already cleared such to even access it. It's literally just there for those who want the challenge or for whom its rewards are still sufficiently efficient (in which case -- decently competent).

I still do old content for fun and no real rewards (and many PUGs) so I don't know what to tell you. And nobody is forcing you to do every roulette anyway.

This. Is it so hard to think that maybe fun could be one's "meat and potatoes" in doing content, especially if there's at least some reward (say, around that of the latest dungeon, despite the obviously longer run times for Unreal)?

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Off-topic:

Coming from WoW, I've seen the complete opposite of this, which is a system that exclusively rewards the best of the best for exclusively running with the best of the best.

Wut? You can PuG +15s (reward caps) even at ilvls around those awarded by +10s. I've done it just fine on four characters now, sure, a premade of particularly good players would allow you to complete a +15 at even lower ilvl, but one's group don't have to be the best of the best to complete (who would be off doing 25s or higher, well past any point of being rewarded for the additional challenge outside of the fun of it), only competent, and you still get the gear rewards even if you fail the timer.

If you're then talking about Mythic raiding, why shouldn't you need a fully competent group to do the most challenging stuff in the game? Heck, it's less exclusive than Ultimate, and is no more exclusive in whom it rewards than literally any content in XIV; if you're there when the content is cleared, you get the same loot opportunities as anyone else, regardless of performance. You wouldn't see so large a run-/clear-/drops-selling economy otherwise.

Master Looter isn't even an option in WoW. Heck, even Need/Greed isn't, so you can't be pressured to pass. It's just Personal Loot. You've a chance to get a spec (i.e., job)-derived drop and if it drops, it goes straight to your bags. One can trade their drops after the fact only if it's not an ilvl upgrade.

[Velnora]

How many failures on the boss that you see every day is still fun? How many times it's fun to wipe to that particular pack of mobs because bard keeps hitting sleeping monster with AoE or tank forgets to interrupt big spell? Because something tells that snapping point comes quicker than you think.

History shows that players rather not engage with the content or leave the game if daily grind gets too hard. It happened in WoW on the release of Cataclysm, it happened in XIV with shinryu, when good players would rather lower their ilvl than wipe with newbies 10 times in a row. And same will happen with hard roulette.

It doesn't need to be incredibly hard. Just something that isn't a mindless *Run down hallway, aoe everything down"