Since the Asymptotes of the Root Locus tends to infinity through angles $(2r-1)\pi/n, r=1..n$, with $n+z$ poles and $z$ zeros, independently if they lie or not at the LHP, if you place the zeros enough far from the poles, and if you use an enough small gain $K$, you can keep the asymptotic shape of the poles only.
Hence, if you have p-multiple poles, for some small gain, they should be located through angles $(2p-1)\pi/4, p=1..4$. and for some large gain, they should be located through angles $(2(p-z)-1)\pi/4, p-z=1..2$.
A simple example would be:
$$
H(s)={1+0.2s+(0.32s)^2 \over (s+1)^4}
$$
This system has $p_{1,2,3,4}=-1$, $z_{1,2}=-1\pm 3i$ and $k_0=1$.
It is Critically Stable for $K\approx 5.8$, at $p_{1,8} \approx \pm i$ for a gain keeping the asymptotic trend of the 4-multiple poles, and for $K\approx 275$, at $p_{1,8}\approx\pm 4i$ for a gain losting the asymptotic trend of that 4-multiple poles.
For an enough large gain, we recover the final asymptotic shape, which in our case, happens just after the closed loop poles reencounter.
As all the zeros and poles were chosen at a fixed imaginary line, the centroid lies in the same line, and the asymptotes angles of the whole feedback system at $\pi/2$ and $3\pi/2$, start as straight lines.

Many more examples can be found following this principle.
If we require to pass 4 times through the positive imaginary axis, then a similar system can be build, for example:
$$
H(s)={(1+0.02s+(0.1s)^2)^3 \over (s+1)^8}
$$
This time we use a 8-multiple poles $p_{1,2,3,4,5,6,7,8}=-1$ and a corresponding 3-multiple complex zeros, this time a bit farther $z_{1,2,3,4,5,6}=-1\pm10i$ than the previous example, for the 8-multiple pole asymptotes shape to appear freely for low gains, and then to recover the overall asymptotes for higher gains.
As the latter case, we have two gains $K\approx 1.9$ and $K\approx 2.6e^{9}$ for a Critically Stable System.
