It's perhaps easier to understand the set of those positions whose flipped versions are not reachable. Suppose all the following are true:
- all pawns, rooks, bishops and knights are on the board
- the a and h pawns have not moved more than one square; the other pawns are at home
- the bishops are at home
Then no bishop or queen has ever moved, and every move has been from a black square to a white square or vice versa. White starts with 8 units on black squares (four pawns, Ra1, Bc1, Ke1 and Ng1). Later, if this count is even, White has made an even number of moves; if odd, odd. The same can be said of Black units on white squares. The sum of these two numbers is the total number of White and Black moves made so far. This total's parity (i.e. whether it's even or odd) determines whose turn it is to move: even, White's turn; odd, Black's turn.
Now flip the position. The total is the same. Therefore the same player must have the move. Thus if, as you require, we must also swap whose turn it is to move, then the resulting position is unreachable.
By contrast, if anything else has happened, one or other player can "lose a move" and enable the flipped position to occur. For example, given that we may play into a Sicilian with White to move, by 1 e4 c5, we may also play into a reversed Sicilian with Black to move, by 1 c3 e5 2 c4. Another example: given that we may play into a Indian with White to move, by 1 d4 Nf6, we may play into a reversed Indian with Black to move, by 1 Nf3 d6 2 Ng1 d5 3 Nf3.
Thanks to Steve Bennett for the idea which leads to the following additional positions. Suppose that at least one of the players retains at least one castling-right, their f-pawn has advanced one square, and (except for the f-pawn) the above conditions all hold. Now flip the position. The only way to reach the flipped board position with the other player to move is to change the parity of the number of moves, by moving this other player's king out via the f-file. But moving their king destroys both their castling-rights, so the position is different.