This is a star domain with respect to the origin by its construction. Because of this reason the nonlinear system $$\begin{cases}x_0 = \lambda(9\sin(2t)+5\sin(3t)),\\y_0= \lambda(9\cos(2t)-5\cos(3t)) \end{cases}$$ has a real solution $\{\lambda,\, t\}$ satisfying the restrictions $\{\lambda \ge 0, \lambda < 1,\, t \ge 0,\, t\le 2\pi\}$ if a point $(x_0,y_0)$ is inside the domain, not belonging to its boundary, and has no such solution in the opposite case. The only working method to solve that system is numeric.
I use the DirectSearch package of Maple to this end. The DirectSearch package should be downloaded from Maple Application Center and installed in your Maple.
Let us begin from the point $A(1,-1)$:
sol := DirectSearch:-SolveEquations([1 = lambda*(9*sin(2*t)+5*sin(3*t)), -1 = lambda*(9*cos(2*t)-5*cos(3*t))], {lambda >= 0, t >= 0, lambda <= 1, t <= 2*Pi}, AllSolutions, solutions = 1);
$$ \left[ \begin {array}{cccc} { 1.32446294720147540\times 10^{-26}}&
\left[ \begin {array}{c} -{ 1.09245945623115402\times 10^{-13}}
\\{ 3.61932706027801032\times 10^{-14}}\end {array}
\right] \\&[\lambda= 0.349055727031787666,t= 1.23742356730272540]&77
\end {array} \right]
$$
This output means the numerical solution $\lambda= 0.349055727031787666,t= 1.23742356730272540$ satisfies the first equation with the accuracy $- 1.09245945623115402\times 10^{-13} $ and the second equation up to $ 3.61932706027801032\times 10^{-14} $. The number $ 1.32446294720147540\times 10^{-26}$ equals the sum of the squared residuals. The number $77$ is the number of steps to solve the system. We see that the point $A$ is placed in the interior of the domain as $\lambda= 0.349055727031787666 < 1.$
Now we consider the point $B(5,5)$:
sol := DirectSearch:-SolveEquations([5 = lambda*(9*sin(2*t)+5*sin(3*t)), 5 = lambda*(9*cos(2*t)-5*cos(3*t))], {lambda >= 0, t >= 0, lambda <= 1, t <= 2*Pi}, AllSolutions, solutions = 1);
$$ \left[ \begin {array}{cccc} 0.804364869871176834& \left[
\begin {array}{c} - 0.0365718874608482736\\
0.896117942526946542\end {array} \right] \\&[\lambda=
0.99999999999280198,t= 0.156602991662910751]&99\end {array} \right]
$$
The above output means the system has no real solution as the residuals are quit big. The SolveEquations command can return not only exact solutions of the equation system but also any minimums of function $$F:=(5 - \lambda(9\sin(2t)+5\sin(3t)))^2+(5 - \lambda(9\cos(2t)-5\cos(3t)))^2.$$ If the residuals too large then the solution is not exact solution but it is only solution that minimizes the residuals. We can draw the conclusion that $B$ does not belong to the interior.
Finally, it should be noted that the winding number does not discriminate the interior points in this situation. See that page of William F. Basener, Topology and Its Applications:
