That doesn't answer the original question, but here are some thoughts regarding the diagonal way:
In nautical terms there exists a word for the approaching speed to a goal, if it is not possible -due to which reasons ever – to sail directly in the preferred direction. It’s called VMG (velocity made good) and can be calculated with the actual boat speed over ground SOG multiplied with the cosine of angle α between the course over ground COG and the direction to the goal.
VMG = SOG ⋅ cos(α)
The larger α, the smaller the VMG and therefore the “approaching velocity” to the goal. Making way, the angle α increases and the VMG decreases (except if you point straight ahead to the goal, i.e. α = 0). The boat stops approaching to the goal, if the α = 90°. The distance Dlim, when this limit is reached can be calculated with the initial angle α0 at t=0.
Dlim = -200 ⋅ cos (α0)
The time tlim till this point is reached (assuming the SOG = -20) can be calculated:
tlim = Dlim / SOG
To answer your question in 3.: If -20 is the SOG and not the (partial) velocity in x-direction (i.e. there is the possibility, that the boat moves “diagonally”), the boat will approach to the origin only till the time tlim, afterwards it will move away (and approaching doesn’t apply for all t<=10).