If you pick a number $x$ randomly from $[0,100]$, we would naturally say that the probability of $x>50$ is $1/2$, right?
This is because we assumed that randomly meant that the experiment was to pick a point from $[0,100]$ (with numbers equally distributed). But, since $f(r)=r^2$ is a bijection $[0,10] \rightarrow [0,100]$, we could also pick a number $r$ from $[0,10]$ and then do $x=r^2 \in [0,100]$ and let that be our random experiment. This time $x>5$ only for $r> \sqrt{50} \sim 7.07$.
In this case we would agree that the first way of choosing $x$ looks a lot more natural. So we would equally agree that is a successful way of modeling the experiment ''pick a random number from [0,100]''.
There are sometimes when we can't even agree on that! For example, on Bertrand's Paradox we are asked to pick a random chord from a circumference and calculate the probability that it is longer than the side of the inscribed equilateral triangle. The point is there are several (a priori) natural ways of choosing the chords (three of them are nicely described here) which, of course, produce different probabilities.
How and when can we consider something is truly random? Does it even make any sense saying something is truly random or is it more a matter of agreement?
Is there any convention in the mathematical community about this issues?
Could we say the common notion of randomness relates to the notion of uniform distribution?
Are there any successful approaches on models about randomness? (That let us decide if a certain distribution represents randomness in the sense of being an uniform distribution)
For example, on the comments it is said: "One can show [using Kolmogorov Complexity] that a number in [0,1] is random with probability 1 under the uniform distribution, so it coheres well with other notions.''
One way to interpret your motivating examples is not that the word random is ill-defined (all of probability theory would disagree with that), but that you want a mathematically natural characterization and generalization of the notion of a uniform distribution. In that case, the answer could be the Haar measure on Lie groups (among other things). This is a measure that is invariant under the action of the group, and if you restrict it to a compact set you can normalize it to form a probability distribution.
For example, the real numbers form a Lie group under addition, and the corresponding Haar measure is nothing but the usual uniform measure on $\mathbb R$, which restricted to $[0,100]$ leads to the uniform distribution on the same. We can tell that the distribution produced by uniformly picking a number in $[0,10]$ and squaring it is not uniform, because it is not invariant under addition (the probability of $[20,30]$ is not equal to the probability of $[20,30]+40 = [60,70]$).
Similarly, when dealing with lines in the plane, the relevant Lie group is the Euclidean group of rigid motions of the plane, which comes equipped with a Haar measure. This induces a measure on the space of lines which is invariant to translation and rotation. When restricted to the lines that intersect a given circle, it gives you something you could objectively call "the" uniform distribution over chords of the circle. This corresponds to picking the angle and the distance from the center uniformly, and matches Jaynes' solution using the principle of maximum ignorance.
The field of integral geometry deals with exactly this sort of thing: the properties of geometrical objects under measures that are invariant to the symmetry group of the geometrical space. It has many interesting results such as the Crofton formula, stating that the length of any curve is proportional to the expected number of times a "random" line intersects it. Of course, this could not be a theorem without precisely formalizing what it means for a line to be random.