Effect of "RUNNING WITH" when the line "run with" stops 

I seek your collective wisdom on an ancient surveying issue.

Southacre  - a ~ rectangular shaped property to the south of Northacre (and conveyed by a common owner 10 years before the conveyance of Northacre) has as its northermost line a line which runs from west to east from one previously established N-S running property line on the west to a known driveway called for in the deed leading to the grantor's house-- an artificial monument on the east -- which makes up the eastern boundary of Southacre.  The distance call of that northerly line is for 100 yards from one monument on the west to the driveway monument on the east. The monuments control the distance so if the measured line called for in the deed actually on the ground runs for only 90 yards, or conversly, might extend beyond the driveway, the monument controls and the line stops at the monument (a driveway) as I understand it.

10 years later, the common owner -- who had earlier conveyed Southacre -- conveys Northacre situated to the north of Southacre. The description of the western line in the Northacre deed runs from the North down the same previously established N-S property line on the west side in a southerly direction  a distance "to the land of Southacre and thence with the land of Southacre in an easterly direction for 152 yards to a Cherry Tree, thence running in a northerly direction ..... " to another  tree and from there around to the point of beginning.

Note that the common grantor at the time of both conveyances owned land on both sides of his driveway.

QUESTION:  We know that that northerly line of Southacre can only extend between the two monuments in Southacre's deed and not beyond or past that second monument (the driveway). When the call in the deed to Northacre says for its southerly line: "runing with the land of Southacre” but gives a distance (152 yards) to a Cherry Tree which is clearly in excess of the distance possibly run by that northerly line of Southacre, does the line of the conveyance of Northacre STOP at the driveway just like the Southacre line of conveyance does?

STATED ANOTHER WAY: When the deed to Northacre says running with a known line (which ends at a driveway), but the distance called for in the second deed is longer than the known "running with" line, does the line of the Northacre southern line also stop at the driveway and thence run North from the same corner, (where there are no Cherry Trees) OR does the line of Northacre continue across and beyond the driveway (Searching for a cherry Tree) a new line of division beyond the driveway on to the east and then run north after running across the Grantor's  open space beyond the driveway?

That “Cherry Tree”  probably no longer exists anywhere that we know of.

If you can give me your views and point me to any authorities on this subject I'd be most grateful. Is this issue settled or is there a minority view that the course "with the lands of Southacre" continues after the lands of Southacre have run out? I am looking for authority that Northacre’s line stops in the same spot (the driveway) as Southacre’s.

Any referral to articles or treatises on the subject --- one way or the other --- would be most helpful.

Thanks much.

Walter