These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
YMMV: Divine Comedy
Ass Pull: At one point, Dante uses a cord around his waist to lower himself and Virgil into a section of Hell. Scholarly opinion is still divided as to whether this cord was actually an Ass Pull or was a result of Dante wearing a Franciscan habit.
Evil Is Cool: Guess what part of the trilogy is overwhelmingly the best-known?
Hilarious in Hindsight: The punishment of corrupt politicians — being trapped in boiling pitch — is especially ironic considering the politics behind oil today.
Moment Of Awesome: The episode of Ulysses' last journey (Hell, 26th canto) is usually regarded as an epic one and one of the best-remembered moments of the whole poem (Men are not thou to live as brutes... etc).
Nightmare Fuel: There's probably at least one Infernal punishment that will tap into a person's primal fears, even if they're not guilty of the associated sin; if they are, maybe it'll Scare 'Em Straight.
If you're just passing through, there's the wood of suicides, where you have to walk through a forest where the trees bleed from every snapped twig and torn leaf. Through the bleeding holes in their wooden flesh, they wail in pain or ask why you're hurting them. And then one of the local denizens comes crashing through, leaving a trail of blood and agony in its wake...
There are two possible meanings to what Ugolino says: Yes, he did OR No, he didn't. The line is fairly ambiguous.
Would he really be in Hell if he didn't do it?
Painful Rhyme: Since terza rima is much harder to pull off in English than in Italian, some translations fall into this.
Unfortunate Implications: In Canto IV of Paradisio, Dante asks Beatrice why the nuns who have been raped (in both the old school meaning as well as [very likely] the contemporary meaning) are placed in the sphere furthest from God's love, to which Beatrice replies that people are complicit in the violence acted upon them.
The most logical view of this is that 1) No life is man's to take, not even his/her own, and 2) suicide is basically murder for which you cannot absolve yourself since you're, you know... dead.
Usury —- lending money and charging interest for it -— will get you into the worst section of the Seventh Circle.
Considering that usury is one of the most despicable ways to exploit people in need, there's not much dissonance about it.
Actually, in medieval times, any interest, not just exploitative interest, was considered a sin. Europe did not start to advance until people ignored this.
Consulting fortune tellers. While it's generally agreed that you shouldn't, most people think of it as a harmless game.
No doubt followers of the Prosperity doctrine would view simony as a virtue rather than a sin.
The example of sowers of discord? Muhammad.
In Dante's Hell, thieves and counterfeiters are regarded as worse sinners than murderers. The First Circle (Limbo) consists of "virtuous pagans" and the unbaptised, whose only real crime is not being Christian. Nowadays, condemning someone to hell for such a fact is generally considered a wee bit harsh.