Including labels in map legend and point symbology of ArcGIS for Desktop?

You can't easily display label information in the legend, so the best solution is to have unique symbology for each of your points. The simplest way to do this is to open the properties for your layer and and select the Categories option on the left hand side (see below). You can then select the field to create a different symbology for each point.

Assuming you want to have show the point with the text inside rather than just using different colours I would start by creating a point for each feature as above. The next step is to select each point by double clicking it to open the symbol selector, and then going to the Edit Symbol button.

In this menu you can build a symbol by adding layers - including characters. The text can be accessed in the Character Marker Symbol menu from in the Type drop-down.

(I would start be editing the symbol so that the symbology is consistent for all of your points then you will just need to manually change the number for each one.)

This should allow you to put a different number in each point on the map and legend whilst also being able to display your description in the legend.

Perhaps you could use the "Unique Values, Many Fields" symbology option and choose the number field then the description field:

Then when you insert the legend it will show the number and the description:

Its not perfect because it doesn't show the number inside the symbol but it might do the trick and I bet if you convert the legent to graphic then do some ungrouping/grouping you could move the symbol underneath the number: