It's the second solution which is correct, and the first one is wrong!
The error hides in the assumption the whole figure is a triangle. If it was, the big triangle would be similar to the smaller one on the right side, hence the proportion would hold
$$\frac{12+13}{11+21}=\frac{15}{21}$$
However, it does not, as
$$\frac{12+13}{11+21}=0.78125 > 0.7142857 \approx \frac{15}{21}$$
and the big figure is a concave quadrangle.
Without loss of generality, suppose $A < B < C < D$.
Notice that if $A \ge 3$, then $B \ge 4$, $C \ge 5$, $D \ge 6$, and then $\tfrac{1}{A}+\tfrac{1}{B}+\tfrac{1}{C}+\tfrac{1}{D} \le \tfrac{1}{3}+\tfrac{1}{4}+\tfrac{1}{5}+\tfrac{1}{6} = \tfrac{19}{20} < 1.1$. So we need $A = 1$ or $A = 2$.
Case 1: $A = 2$. Then we need $\tfrac{1}{B}+\tfrac{1}{C}+\tfrac{1}{D} = \tfrac{3}{5}$ with $2 < B < C < D$.
Since $\tfrac{3}{B} > \tfrac{1}{B}+\tfrac{1}{C}+\tfrac{1}{D} = \tfrac{3}{5}$, we must have $B < 5$, i.e. $B = 3$ or $B = 4$.
If $B = 4$, we need $\tfrac{1}{C}+\tfrac{1}{D} = \tfrac{7}{20}$ with $4 < C < D$. Since $\tfrac{2}{C} > \tfrac{1}{C}+\tfrac{1}{D} = \tfrac{7}{20}$, we must have $C < \tfrac{40}{7}$, i.e. $C \le 5$. Since $4 < C \le 5$, we must have $C = 5$, but then $D = \tfrac{20}{3}$, which is not an integer. So there are no solutions with $A = 2$ and $B = 4$.
If $B = 3$, we need $\tfrac{1}{C}+\tfrac{1}{D} = \tfrac{4}{15}$ with $3 < C < D$. Since $\tfrac{2}{C} > \tfrac{1}{C}+\tfrac{1}{D} = \tfrac{4}{15}$, we must have $C < \tfrac{15}{2}$, i.e. $C \le 7$. Testing $C = 4, 5, 6, 7$ yields $D = 60, 15, 10, \tfrac{105}{13}$ respectively. In this case, the smallest sum where $C$ and $D$ are integers is $21$ which occurs for $(A,B,C,D) = (2,3,6,10)$.
Case 2: $A = 1$. Then, we need $\tfrac{1}{B}+\tfrac{1}{C}+\tfrac{1}{D} = \tfrac{1}{10}$. But since $\tfrac{3}{D} < \tfrac{1}{B}+\tfrac{1}{C}+\tfrac{1}{D} = \tfrac{1}{10}$, any solution in this case will have $D > 30$, and thus, $A+B+C+D > 30 > 21$. So we will not find a smaller sum in this case.
Therefore, the minimum sum is $21$.
Note that if you just need to get an answer quickly without a rigorous proof, then you can probably just guess and check until you find something reasonably small. In problems with Egyptian fractions (fractions with numerator $1$), the sum $\tfrac{1}{2}+\tfrac{1}{3}+\tfrac{1}{6} = 1$ comes up a lot, namely it is the smallest set of distinct Egyptian fractions that add up to $1$. So it's not too hard to build off of that to get $\tfrac{1}{2}+\tfrac{1}{3}+\tfrac{1}{6}+\tfrac{1}{10} = \tfrac{11}{10}$. I'm not sure if there is an easy way to convince yourself that's the smallest sum though.
Best Answer
The lower shaded sector can be seen, by parallel lines and symmetry, to complement the larger shaded sector in the top right to form a full quarter circle, of area $\pi/4$. The remaining sector is half, because we have squares and the diagonal makes a $45^\circ$ angle, of a quarter circle so it has area $\pi/8$.
Together the shaded area makes $\frac{3}{8}\pi$.
As for tips, I personally dislike classical geometry and tend to do its problems with great reluctance when in a maths challenge (maths challenges love these problems for some reason!). However, maths challenges worth their salt always will go for problems, whether in geometry or not, that can be solved using a shortcut change in perspective. Here the trick was to see the shaded areas complement each other; harder questions will have a similar trick, but not one that geometrically annoyed people like myself can see very well! If the problem looks intractable, it usually will be in these challenges bar the hidden shortcut.