Any ideas on if ArcMap is able to create labeling similar to this map? Ie. 95xx or 9500 is listed outside of the units and the the actual last 2 digits are listed within so that each unit does not have 4 digits labeling inside?
You can accomplish labeling the LAST two digits using label expressions for your parcel layers.
Your expression would look something like this in VB:
Right ( [Field], 2 )
Or you can use maplex labeling engine to abbreviate the labels
To label the FIRST two digits you could set up an additional field with the area of the parcel, so that if it's below a certain area it will truncate the labels to your specification (using either maplex or the label expressions above). From there you could place the remaining label (for the block) as ANNOTATION on the blocks where the labels are truncated.
You could also fool around with boundary based labeling for each block. It all depends on how your data is set up!
As GISKid states, it depends on how your data is set up.
Based on your other questions, no, there is no straight labeling scheme available that would do what you want. Any solution is going to involve modifying or creating new data. In this case you would need to create an aggregate polygon of each contiguous building poly with an attribute that has the building number (unless you already have that - without specific details or examples of your data we cannot give specific, readily-applicable solutions).
You would then utilize label expressions to label the individual building polys with the last x digits constrained to the interior, and label your new aggregate polys with the first x digits constrained to the exterior.
The only way I could see this happening is to select everything with 4 digits (or more) and export, from the exported feature class calculate the first len([field])-2 into a field and the last two into another field. Dissolve the export by first digits and label as [first_digits] & "xx" to get the outside label and then label each of the smaller blocks with the last two digits. Of course these would need to be excluded from the original boundaries but would give you most of what you want.
Unfortunately this is not an on-the-fly solution, but more of a data exercise - but that's the essence of GIS.
In the end you would be displaying 3 feature classes: 1. Features with less than 4 digits 2. The dissolved first digits features 3. The features with 4 digits labelled by their last two.