Recall that exponential distributions are memory-less. Therefore, at the time when the first of Jake and Naomi get done with their service, Paul would go to the server that becomes empty. Say he goes to server 1 at time $t=s$. Then, due to memoryless property, $\mathbb{P}[X_2>t+s|X_2>s] = \mathbb{P}[X_2>t]$. Thus, we are comparing the distributions for $X_1$ and $X_2$ afresh.
Concretely, let $\lambda_1 = \frac{1}{3}, \lambda_2 = \frac{1}{5}$. Then $\lambda_{min(1,2)} = \lambda_1 + \lambda_2 = \frac{8}{15}$ (See linked question)
Thus the expected time at which Paul enters the service is $T_{entry} = \frac{1}{\lambda_{min(1,2)}} = \frac{15}{8}$
Now for part A there are two cases as you have pointed out. $\mathbb{P}[M=X_1] = \frac{\lambda_1}{\lambda_1+\lambda_2}=\frac{5}{8}$ and $\mathbb{P}[M=X_2]=\frac{3}{8}$
If $M=X_1$, then time taken for Paul to finish service in expectation is $\mathbb{E}[T_{total|M=X_1}] = T_{entry} + \frac{1}{\lambda_1} = \frac{15}{8} + 3 = \frac{39}{8}$
Similarly, $\mathbb{E}[T_{total|M=X_2}] = T_{entry} + \frac{1}{\lambda_2} = \frac{15}{8} + 5 = \frac{55}{8}$
Finally we have by iterated expectation, $\mathbb{E}[T_{total}] = \mathbb{E}_M\big[\mathbb{E}_{T|M}[T_{total}|M=X_i]\big] = \frac{5}{8}\cdot\frac{39}{8}+\frac{3}{8}\cdot\frac{55}{8}=\frac{45}{8}$
For part B, we again have two cases. If $M=X_1$ in the first iteration when Paul enters the system, then $M=X_2$ in the second iteration for Paul to finish last. Similarly, if $M=X_2$ in the first iteration, then $M=X_1$ in the second iteration. The total probability of this happening is
$\mathbb{P}(\text{Paul finishes last}) = \frac{\lambda_1}{\lambda_1+\lambda_2}\cdot \frac{\lambda_2}{\lambda_1+\lambda_2}+\frac{\lambda_2}{\lambda_1+\lambda_2}\cdot \frac{\lambda_1}{\lambda_1+\lambda_2} = \frac{2\lambda_1\lambda_2}{(\lambda_1+\lambda_2)^2} = \frac{\frac{2}{15}}{(\frac{8}{15})^2} = \frac{15}{32}$