A Timeless Challenge

I've been thinking of stuff to do during this lull at the end of xpac, and challenge modes I find interesting. The premise is that skill>gear. This may be a facepalmingly obvious statement, but I wonder how many actually apply this premise across all parts of the game.

Someone on twitter asked this morning "Is LFR bad because of laziness or stupidity?", and I was reminded of a Greedy Goblin post, About M&S, which got me re-reading Gevlon's other posts, like The Myth of Gear. Short story for those that don't know, Gevlon started a raid called Undergeared which only equipped blue items with no epic gems, expensive enchants, or exalted shoulder enchants. They cleared ICC 5man Heroics, Ulduar, ToT, Onyxia, and most of ICC.

I've also been hearing complaints about people in SoO LFR, or even ToT LFR only having Timeless gear. This is the new "LFM Lower Spire 5k gs required". I'm just tired of hearing it.

As such, I think this undergeared concept can be updated to the new stuff fairly easily, and probably cheaper. Unfortunately there are already guilds named <Timeless> and <Undergeared> on Proudmoore, so I went with <Skilled> which might seem a bit presumptuous, but it is the goal to prove skill is much, much better than gear.

Allowed gear will be:
496 Timeless gear plus 1 535 item (the one guaranteed Burning Ember),
Timeless weapons (476 now, will be 489).
Justice gear, including Dominance Offensive.
450-463 blues.

Prohibited gear will be:
Any raid gear, at any difficulty level.
Legendary capes.
Valor gear.
Gear dropped off world bosses.
Seasonal items.
BoE items.

My goal is to put together at least 10 people who can commit to the concept to raid Flex SoO 1 night a week.

Any thoughts?

A few clarifications needed on gear -

Legendary Metas
Timeless Isle 535 trinket
Valor Upgrades
Justice Upgrades

You mention about forming a guild with the players but as the target is Flex SoO I don't see why you don't do it cross realm, removing the need for players to level.

Good points, thanks.

No legendary anything.
I was thinking maybe allowing 1 535 trinket. 50k coins is a bit of a grind though, not an automatic gimmie, and it would raise the average ilevel of the player up even more, reducing the challenge. I'm not certain about this point.
No Valor upgrades, since that's a grind not accessible to a new 90. Maybe 4 upgrades allowed to match 1 weeks worth of valor.
Justice upgrades are easy, so for sure allowed, probably required.

About the Guild being formed, I want to have credit given to a particular entity for both challenge mode and raid achievements. I'll start off recruiting in OpenRaid, of course, but I'll focus on getting at least 8 Proudmoore players downing bosses in SoO and teams of 3+ doing challenge modes.

I'm combining this raiding challenge with a challenge mode themed guild because I think the right mentality is needed for both. Gear doesn't matter nearly as much as proper execution. Getting loot does not matter at all, compared to getting the achievement.