You are correct that this is a very subtle question, known as the Borel–Kolmogorov paradox. As Kolmogorov wrote:
The concept of a conditional probability with regard to an isolated hypothesis whose probability equals $0$ is inadmissible.
An indication that the naively computed conditional probability is ill-defined is that a nonlinear transformation of the variables may give inconsistent answers.
The resolution is that conditional probability should be defined in terms of a condition with finite probability. A limit may then be taken where the probability goes to zero, but the exact choice of condition may affect this limit, just as the value of a general indeterminate form $0/0$ may depend on how the limit is taken.
Intuitively, when we condition on a 1D subset of a 2D space, we need to specify not merely a curve but a "relative thickness" along the curve. This is a necessary input for the problem to be well-defined. Then, if we properly account for this thickness during a nonlinear transformation of variables, the conditional probability remains consistent.
In your example, the bird landing on the line $Y = 2$ can only be physically observed to some finite precision. The nontrivial implicit assumption being made in your example is that the precision with which $Y$ is observed is independent of the value of $X$. (Michael's answer denotes this precision by $\delta$ but does not explain the importance of the assumption.)
If the assumption holds for this choice of variables (Cartesian coordinates), it will not hold if we reparametrize $Y$ with a different coordinate, say $Y' = (Y - 2)/(X + 1)$. It is true that $Y = 2 \Leftrightarrow Y' = 0$, i.e., both describe the same line, but the densities along that line are non-trivially different: $f_{X,Y}(x, 2) = 1/50$ and $f_{X,Y'}(x, 0) = (x + 1)/50$.
A physical motivation for this $Y'$ is to imagine that you are standing outside the grassy region, at $(x, y) = (-1, 2)$. Then $Y'$ represents your line of sight to the bird. It's plausible that you have a fixed angular acuity in your observation, so you'd actually have an $X$-independent precision in $Y'$ rather than in $Y$. So in this case, we get a well-defined but different answer: Conditional on observing $Y' = 0$, the probability that $0 \le X \le 5$ is $7/16$, which is less than $5/8$. This makes sense: There's a lower probability for the bird to be at small $X$, because if it's at large $X$ (farther from you) it can more easily "appear" to be on the line $Y = 2 \Leftrightarrow Y' = 0$.
Of course, we can also solve the "line of sight" version in the original Cartesian coordinates $(X, Y)$ if we account for the "thickness" factor mentioned above. We are conditioning on a wedge rather than a rectangle around $Y = 2$, and this non-uniformity has an effect on the conditional probability that persists even when we take the limit of an extremely precise observation where the wedge and rectangle both shrink to a line.