Maybe the following meets your request for the use of Probability
. (This approach is essentially shamelessly stealing from @yarchik 's answer.)
Consider dividing the triangle into 3 equal parts and focus on the lower triangle:
triangle = ListPlot[{{-1/2, 0}, {1/2, 0}, {0, Tan[π/3]/2}, {-1/2, 0}},
Joined -> True, PlotRangeClipping -> False, AspectRatio -> Tan[π/3]/2,
PlotRange -> {{-1/2, 1/2}, {0, Tan[π/3]/2}}];
lowersubTriangle = ListPlot[{{-1/2, 0}, {1/2, 0}, {0, Tan[π/6]/2}, {-1/2, 0}},
PlotStyle -> Red, Joined -> True];
Show[triangle, lowersubTriangle]

Now calculate the squares of the distances of a random point to the center of mass (the peak of the lower triangle) and the floor of the lower triangle. We want to know the probability that d2com < d2floor
.
(* Square of distance to center of mass*)
d2com = (x - 0)^2 + (y - Tan[π/6]/2)^2;
(* Square of distance to floor of triangle *)
d2floor = y^2;
We sample uniformly in a rectangle that surrounds the lower triangle and account for the fact that we're only interested in half of the area of that rectangle by restricting the points to the lower triangle:
restrictions = y < (x + 1/2) Tan[π/6] && y < (1/2 - x) Tan[π/6];
probability = 2 Probability[d2com < d2floor && restrictions,
{x \[Distributed] UniformDistribution[{-1/2, 1/2}],
y \[Distributed] UniformDistribution[{0, Tan[π/6]/2}]}]
(* 5/27 *)
DirichletDistribution[]
is the appropriate distribution for sampling uniformly within a simplex (in your particular case, an equilateral triangle). You can use this as a starting point. $\endgroup$