As 2.x takes longer as planned, I added the SpeechbubbleContainer and StepLabelContainer (Enumerable label) to the 1.2 branch. This code was stored somewhere on my hard-drive, is still experimental.

Greenshot/Drawing/StepLabelContainer.cs

@@ -0,0 +1,81 @@
+/*
+ * Greenshot - a free and open source screenshot tool
+ * Copyright (C) 2007-2012  Thomas Braun, Jens Klingen, Robin Krom
+ * 
+ * For more information see: http://getgreenshot.org/
+ * The Greenshot project is hosted on Sourceforge: http://sourceforge.net/projects/greenshot/
+ * 
+ * This program is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU General Public License as published by
+ * the Free Software Foundation, either version 1 of the License, or
+ * (at your option) any later version.
+ * 
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU General Public License for more details.
+ * 
+ * You should have received a copy of the GNU General Public License
+ * along with this program.  If not, see <http://www.gnu.org/licenses/>.
+ */
+
+using Greenshot.Drawing.Fields;
+using Greenshot.Helpers;
+using Greenshot.Plugin.Drawing;
+using System;
+using System.Collections.Generic;
+using System.Drawing;
+using System.Drawing.Drawing2D;
+
+namespace Greenshot.Drawing {
+	/// <summary>
+	/// Description of StepLabelContainer.
+	/// This is an enumerated label, every single StepLabelContainer shows the number of the order it was created.
+	/// To make sure that deleting recalculates, we check the location before every draw.
+	/// </summary>
+	[Serializable()]
+	public class StepLabelContainer : TextContainer {
+		public StepLabelContainer(Surface parent) : base(parent) {
+			_defaultEditMode = EditStatus.IDLE;
+			parent.StepContainers.AddLast(this);
+			// Set defaults
+			Width = 40;
+			Height = 40;
+		}
+
+		public override void Dispose() {
+			Parent.StepContainers.Remove(this);
+			base.Dispose();
+		}
+
+		/// <summary>
+		/// We set our own field values
+		/// </summary>
+		protected override void InitializeFields() {
+			AddField(GetType(), FieldType.LINE_COLOR, Color.White);
+			AddField(GetType(), FieldType.FILL_COLOR, Color.DarkRed);
+			AddField(GetType(), FieldType.FONT_SIZE, 21f);
+			AddField(GetType(), FieldType.LINE_THICKNESS, 0);
+			base.InitializeFields();
+		}
+
+		/// <summary>
+		/// Override the parent, calculate the label number, than draw
+		/// </summary>
+		/// <param name="graphics"></param>
+		/// <param name="rm"></param>
+		public override void Draw(Graphics graphics, RenderMode rm) {
+			int number = 1;
+			foreach (StepLabelContainer possibleThis in Parent.StepContainers) {
+				if (possibleThis == this) {
+					break;
+				}
+				if (Parent.IsOnSurface(possibleThis)) {
+					number++;
+				}
+			}
+			this.Text = number.ToString();
+			base.Draw(graphics, rm);
+		}
+	}
+}