Eric,
I'll have a look at the data later today when I get back to my GIS machine.
If the Resource Center imagery is clear enough, make the parcels show just outlines and you might be able to get a better feel for which shapefile is more accurate. One presumes that more recent photo coverage and mosaicing should be more accurate than older stuff that might not have been set up for the world of GIS parcel fabrics.
Given the precision you need for this, and the available resolution on the Resource Center you could go back to overlaying both shapefiles in Google Earth, but make the parcel polygons clear so you can see alignment better. The May 2010 GE image looks high enough resolution to draw from itself as you can see sidewalks and fence lines.
Another essential place to check would be with Pembroke city engineering for CAD drawings based on surveys. You'd have to georeference these dxfs in ArcMAP by finding two unambiguous points for which you have independent coordinates.
The photomosaic/orthophotos will have ground control points with precise coordinates and you could also cross check those both against the display in ArcMap and in Google Earth to see if there is any glaring discrepancy assuming the GE imagery is correctly georeferenced. Overall you are trying to check the veracity of the new orthophoto mosaics; from what I can see the new digitizing is good relative to them. So the 3 to 5 m shift you measured relative to GE spot locations in the new shapefile (and presumably imagery) is cause for concern. GE imagery might be off by that much, but the city engineering drawings will not. Another independent check would be some GPS coordinates of distinct features on the new orthophotos, but those would have to be taken with a sub meter unit (e.g. Trimble GeoXT) not just a recreational one (e.g. Garmin Map60CSx). If it came to that you could also have the control points checked, but I would not hold much hope that they were inaccurately measured. Maybe a wrong transformation from WGS84 to NAD83, for the control point file, but that would not account for much.
Meanwhile one thing I noticed that might help with the connection problem is that you seem to have a space in the name of the personal geodatabase in C:\Drawings\Pembroke2\Pembroke DB.mdb, which is not advisable. If so, good idea to either rename or copy contents to a new one. Also, I generally no longer use .mdbs in favour of file geodatabases after finding problems with them moving from an XP platform to Win7, but I don't think that is a cause of the connection problem.
Hardolph