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Number is just a mean to defeat more bosses, it goes up very slowly the first time around but as you unlock features, get stronger gear and get more energy and magic stats you will be able to rise from the start all the way to whatever boss you were at in a few days at most (and just getting far enough to re-unlock whatever adventure zone you need to farm is often reached in a day or less).
That being said, challenges are better left for when you can clear them much faster, it makes clearing the challenges much quicker and the climb after that is also significantly faster.
The main point of challenges is not the exp or AP (except the 24h challenge that gives a large amoutn of AP for later clears) but the specific bonuses they give, like the bonus to adventure stats with the basic challenge.
And if you've spent those first 100hrs well you will get back in 3-4hrs. Your gear, energy/magic (which means augments/time machine) persist and those are your true progress. Not a number even if it looked that way until now :)
Megaland is a zone where for the first time you will do multiday run to farm it, along with a 4th titan. You will need seweral hours in time machine and advanced training. It's the point where early phase of the game begins as from this point on you will need to develop your own strategies and choose how to distribute resources and gear.
Good luck :)
Also make good use of Advanced Training, using that helps a lot later. You will want to get at least (almost) all the first page items on the items list apart from boosts maxed before you do more challenges. There will be a time when you hit a wall, even with equipment, advanced training and other unlocks. That is when you should do lots of challenges.
tl;dr: You can (but don't have to) do the Basic Challenge and 24 Hour Challenge (unlocked if you beat the Basic Challenge within a day) early at least once. But afterwards, wait until you hit a wall much much later in the game, at which point you can do most challenges pretty fast.
As you reached boss 100, you are way past the point where you could have done the challenges once reasonably. My advice would be: Max out your items, then get items from higher zones. Use Advanced Training (you don't need to use perk points for that perk yet), and progress naturally until you hit a wall and can do challenges pretty fast. Especially with Advanced Training, you will very soon be able to defeat JAKE and unlock something very useful from his drop. That is the point when item maxing becomes a must do for the drop chance bonus from the maxed Clockwork and 2D sets.
There is one challenge that will not reset your number, but that one explicitly tells you so (you will unlock it much later). All others do reset your number, even if they don't mention it in the description.
But what might be missing is making those buttons green until people read them for the first time.