Solution:
We call checked any square chosen by the Bear, and all its unit squares. The position of a unit square in the table can be defined by the numbers of its row and column, that is, the square (x,y) is in the x-th row and y-th column.
First we prove that 26732−1 questions is enough even on a 2019×2019 table. Let us divide this table into 3×3 squares and apply chess colouring to these large squares so that the corners are white. Then it is enough to check all the black 3×3 squares: no row or column contains four consecutive white squares.
To prove that we need so many questions, we select all the unit squares with coordinates (3m+1,3n+1), where 0⩽m,n⩽672. A 3×3 square obviously can not contain two selected unit squares. On the other hand, if two selected squares lie at distance 3 (i.e., one of them is (x,y), and another is (x,y+3) or (x+3,y)), the Bear must check at least one of these two squares (because if neither is checked, then so are the two unit squares between them, and the Crocodile can place his rectangle on the unchecked squares).
Thus it is enough to produce 26732−1 pairs of selected unit squares at distance 3. One can take pairs (6k+1,3n+1), (6k+4,3n+1), 0⩽k⩽335, 0⩽n⩽672, and (2017,6n+1), (2017,6n+4), 0⩽n⩽335.