Did some dirty numbers to support what I was thinking in my head and came up with this, I did not include ifrit/garuda/titan trials in the calculations so it's not quite right but the point remains the same.
If you as a level 50 join the duty roulette and get matched with 3 other roulette users of evenly distributed levels between 15-50 and then the roulette finder chooses a dungeon at random from the available content to your groups level range your chances of getting each is as follows:
31.10822386% - Sastasha Seagrot*(level 15 - 18)
23.00422866% - Tam-Tara Deepcroft*(Level 16 - 19)
19.1772825% - Copperbell Mines*(Level 17 - 20)
12.380729% - Halatali*(Level 20 - 23)
6.964491002% - Thousand Maws of Toto-Rak*(Level 24 - 27)
3.742611716% - Haukke Manor*(Level 28 - 31)
1.846464025% - Brayflox's Longstop*(Level 32 - 34)
1.000454325% - The Sunken Temple of Qarn*(Level 35 - 37)
0.491677318% - Cutter's Cry*(Level 38 - 40)
0.206612161% - The Stone Vigil*(Level 41 - 43)
0.065794259% - Dzemael Darkhold*(Level 44 - 46)
0.011431184% - The Aurum Vale*(Level 47 - 49)
Note that this is only the case from your personal perspective and when all 4 members joined through roulette.
If I added Ifrit to the equation it would have the same chance as Halatali and steal percentages from all the other content further pushing the 90% of groups to sub-24 content. Other trials wouldn't do much considering their higher level.
First thing you could do to improve this is to have the roulette automatically choose the highest level content that's valid for your group. That would improve the distribution to be more along the lines of this(again trials would skew it some more):
Sastasha - 8.103995199%
Tam-Tara - 7.653892318%
Copperbell - 20.38966049%
Halatali - 21.66495199%
Toto-Rak - 16.10939643%
Haukke Manor - 11.37688615%
Brayflox's Longstop - 5.922067901%
The Sunken Temple of Qarn - 4.070216049%
Cutter's Cry - 2.56558642%
The Stone Vigil - 1.408179012%
Dzemael Darkhold - 0.597993827%
The Aurum Vale - 0.137174211%
Still suffers from the lowest level dictating content, which hurts percent chance of later instances, but it's not nearly as skewed as it currently is.
The other thing that needs to be done is ensuring that 4 random roulette people are never placed together when there is an option of placing them with people that have already directly queued for content. I don't know if it's doing this, I feel like it was supposed to do this, I believe if it is it isn't doing it well. Obviously I don't have any proof of this, but it would be nice to have assurance on it.