This is not a complete answer to (a), but it may be a start. It also explains the repeated eigenvalues.
It is known that a circulant matrix is diagonalized by the Fourier matrix and the eigenvalues of a circulant matrix are given by the discrete Fourier transform of its first row. See chapter 3 of here for a detailed explanation.
Let $c_j$ be the first row your matrix. Given the definition of $\Lambda$, we have
$$
c_j = \begin{cases} 2n(n+1)/3, & j = 0 \\[6pt]
\frac{-1}{1-\cos(\frac{2\pi j}{2n+1})}, & j = 1, \dots, 2n \\
\end{cases}
$$
Let $\lambda_m$ be the eigenvalues of $\Lambda$. Then
$$
\begin{align}
\lambda_m &= \sum_{j=0}^{2n}c_j \exp \left( -\frac{2\pi imj}{2n+1} \right) \\
&= \frac{2n(n+1)}{3} + \sum_{j=1}^{2n} c_j \exp \left( -\frac{2\pi imj}{2n+1} \right), \qquad m = 0, \dots, 2n
\end{align}
$$
The imaginary part of this sum will vanish, so we're left with
$$
\lambda_m = \frac{2n(n+1)}{3} + \sum_{j=1}^{2n} \frac{\cos(\frac{2\pi jm}{2n+1})}{\cos(\frac{2\pi j}{2n+1})-1}
$$
A closed form evaluation for this sum will solve the problem. I don't have any headway on this, but here are two observations.
Observation 1 $ \qquad \lambda_0 = 0$
Proof
$$
\begin{align}
\lambda_0 &= \frac{2n(n+1)}{3} + \sum_{j=1}^{2n} \frac{1}{\cos(\frac{2\pi j}{2n+1}) - 1}\\
&= \frac{2n(n+1)}{3} -\frac{1}{2} \sum_{j=1}^{2n} \csc^2(\frac{\pi j}{2n+1}) \\
&= \frac{2n(n+1)}{3} -\frac{1}{2} \frac{1}{3} ((2n+1)^2 -1) \\
&= \frac{2n(n+1)}{3} - \frac{1}{6} (4n^2 + 4n) \\
&= 0
\end{align}
$$
In the first equality above, I've used the double angle identity, $sin^2(\theta) = \frac{1}{2}(1-cos(2\theta))$, and in the second the identity $\sum_{k=1}^{n-1} csc^2(\frac{k\pi}{n}) = \frac{1}{3}(n^2 - 1)$, see proof below.
Observation 2 $\qquad \lambda_m = \lambda_{2n + 1 - m}$
Proof
$$
\lambda_m = \frac{2n(n+1)}{3} + \sum_{j=1}^{2n} \frac{\cos(\frac{2\pi jm}{2n+1})}{\cos(\frac{2\pi j}{2n+1})-1}
$$
$$
\lambda_{2n + 1 - m} = \frac{2n(n+1)}{3} + \sum_{j=1}^{2n} \frac{\cos(\frac{2\pi j(2n + 1 - m)}{2n+1})}{\cos(\frac{2\pi j}{2n+1})-1}
$$
The denominators in the fractions are the same. The result then follows by noticing that
$$
\begin{align}
\cos \left( \frac{2\pi j (2n + 1 -m )}{2n+1} \right) &= \cos \left( 2\pi j - \frac{2\pi j m}{2n+1} \right) \\
&= \cos \left( \frac{2\pi jm}{2n+1} \right)
\end{align}
$$
Proof of $\sum_{k=1}^{n-1} csc^2(\frac{k\pi}{n}) = \frac{1}{3}(n^2 - 1)$
This proof follows exercise 8 in chapter 5 of Stromberg, An Introduction to Classical Real Analysis.
Begin with De Moivre's formula:
$$
\cos(nx) + i\sin(nx) = (\cos(x) + i\sin(x))^n
$$
Expanding the RHS via the Binomial Theorem gives $$ \cos(nx) + i\sin(nx) = \sum_{k=0}^{n}\binom{n}{k}\cos ^{n-k}(x) (i\sin(x))^k $$
Equate imaginary parts, the RHS is imaginary for $k$ odd, so set $k = 2j+1$
$$ \sin(nx) = \sum_{j=0}^{\lfloor{\frac{n-1}{2}} \rfloor}(-1)^j\binom{n}{2j+1}\cos ^{n-2j-1}(x)\sin ^{2j+1}(x)$$
Setting $n = 2m+1$ and multiplying outside the sum by $\sin ^{2m}(x)$ and dividing on the inside gives
$$ \begin{align} \sin((2m+1)x)
=& \sin ^{2m+1}(x)\sum_{j=0}^{m} (-1)^j\binom{2m+1}{2j+1}\cos ^{2(m-j)}(x)\sin ^{2(j-m)}(x) \\
=& \sin ^{2m+1}(x)\sum_{j=0}^{m} (-1)^j\binom{2m+1}{2j+1}(\cot ^2(x))^{m-j}
\end{align}
$$
Now $\sin((2m+1)x)$ has roots $x = \frac{k\pi}{{2m+1}}, k = 1, \dots, m$. This implies that the polynomial
$$ \sum_{j=0}^{m} (-1)^j\binom{2m+1}{2j+1}t^{m-j} $$ has roots $t = \cot ^2(\frac{k\pi}{2m+1}), k = 1 \dots m$. The sum of the roots of a polynomial of degree $m$ is equal to the negative of the coefficient of the $(m-1)$ degree term divided by the coefficient of the leading term. The leading term has coefficient $2m+1$, the $m-1$ degree term has coefficient $-\binom{2m+1}{3}$, thus the sum of the roots is $m(2m-1)/3$ and we have the identity
$$ \sum_{k=1}^{m}\cot^2 \left( \frac{k\pi}{2m+1} \right) = \frac{m(2m-1)}{3} $$
Making the substitution $\csc^2 \theta = 1 + \cot ^2 \theta$ gives
$$ \sum_{k=1}^{m} \csc^2 \left(\frac{k\pi}{2m+1} \right) = \frac{2}{3}m(m+1) \tag{1}$$
The statement to prove is $$ \sum_{k=1}^{n-1} \csc^2 \left(\frac{k\pi}{n} \right) = \frac{1}{3}(n^2 - 1) \tag{2}$$
Making the substitution $n \rightarrow 2n + 1$, (2) is equivalent to $$ \sum_{k=1}^{2n} \csc^2 \left(\frac{k\pi}{2n + 1} \right) = \frac{4}{3}n(n+1) \tag{3}$$
Noticing that $\csc\left(\frac{k\pi}{2n+1}\right) = \csc\left(\frac{(2n+1-k)\pi}{2n+1}\right)$, we have that the sum over the first $n$ indices in $(3)$ equals the sum over last $n$ indices and thus that $(1)$ is equivalent to $(3)$. $\Box$