I've followed the development of the rules with interest, from the first slipcase edition, then Revised, Cubicle 7:s snippets of information for their version of 2e and now the Free League version and what we know about the changed rules from the kickstarter, Q&A and actual play with Francesco clarifying. We've played since 2013, our campaign are closing in on a hundred sessions.
One thing that has been very clear with TOR is that skill rolls (for common skills, not addressing combat here) are not much of an issue as soon as you've been through your first adventures. The target number (TN) of 14 is easy to reach as soon as you have 3 levels in the appropriate skill. With the Feat die added to that the medium roll lets you reach TN 14 without additional use of Hope or other effects. As soon as your skill level reaches 4 and beyond (5 or 6) it's almost impossible to fail; for the heroes in my campaign it' a matter of how well they succeed, not if they'll succeed. A result less than Greater is considered a failure at our table, almost. Being Weary can change that sometimes, and is a feared state, but it's a rare condition that affects maybe one in ten rolls. You can always raise the TN as a LM, but 16 or even 18 doesn't change this fact much. Nothing wrong with that, and I am of the opinion that players should succeed most of the time, but the effect is that players succeed on every roll, almost never accrue shadow points (an effect that comes with high Wisdom), never needs to use their Hope etc.
And, with additional changes coming up, it seems that skill rolls will be even easier to succeed on. The change from TN 14 to TN (18-attribute level) will lower the TN somewhat, to 13-14 for standard attribute values, if 14 remains the sum of a heroic culture's three attribute numbers. Upon that we will have Favoured rolls (the feat die rolled twice), a mechanic that has existed in some forms already but seems to be more common. Even easier will the rolls be with the addition of an extra die from invoking a Trait. Finally Hope will add 1-2 dice (before the roll instead of adding attribute value after the roll). So far there have been no mentions of preliminary rolls (those exist in 1e, padding's bonus dice before Journeys, Encounters or Battles) but those could possibly add even more dice.
Don't get me wrong, I love the game and I'm very excited for 2e, but a feel there's a risk of inflation in the dice added to a skill roll, while the TN is the same or even lower than before. Skill roll should be challenging even for more experienced heroes, not only for complete beginners. Reading what I have so far, I have some concerns about how the new additions will make skill rolls too easy for characters with some xp under their belts.