Since this is a painted custom control, I think it might be easier to just have a variable hold the last shown tip, and instead of always "setting" the tooltip, just show it.
Simple example (using just a form):
public partial class Form1 : Form {
private List<TipRect> _Tips = new List<TipRect>();
private TipRect _LastTip;
private ToolTip _tooltip = new ToolTip();
public Form1() {
InitializeComponent();
_Tips.Add(new TipRect(new Rectangle(32, 32, 32, 32), "Tip #1"));
_Tips.Add(new TipRect(new Rectangle(100, 100, 32, 32), "Tip #2"));
}
private void Form1_Paint(object sender, PaintEventArgs e) {
foreach (TipRect tr in _Tips)
e.Graphics.FillRectangle(Brushes.Red, tr.Rect);
}
private void Form1_MouseMove(object sender, MouseEventArgs e) {
TipRect checkTip = GetTip(e.Location);
if (checkTip == null) {
_LastTip = null;
_tooltip.Hide(this);
} else {
if (checkTip != _LastTip) {
_LastTip = checkTip;
_tooltip.Show(checkTip.Text, this, e.Location.X + 10, e.Location.Y + 10, 1000);
}
}
}
private TipRect GetTip(Point p) {
TipRect value = null;
foreach (TipRect tr in _Tips) {
if (tr.Rect.Contains(p))
value = tr;
}
return value;
}
}
Here is the TipRect class I created to simulate whatever your PlannedItem class is:
public class TipRect {
public Rectangle Rect;
public string Text;
public TipRect(Rectangle r, string text) {
Rect = r;
Text = text;
}
}