I just love taking shortcuts through entire blocks, especially when walking. An ideal map shall facilitate that by clearly indicating any closed areas.
And I think it's better to overdo than to deliver a false promise: later someone else will map any holes that are lawfully used by locals.
Most private lots are diligently closed from public spaces and areas around high-rise buildings. But, won't the map be too crowded with all those fences? Indeed the fences that delimit one private lot from another -- though they might be visible in satellite photos, too -- have no practical use on the map. Only the perimeter is important.
The last changeset that implements aforementioned ideas rendered as expected and looks nice. Surely not too crowded. On the other hand, the entire block is rather gratifying in that regard. Another block that I've drawn from Bing on Saturday, consists almost entirely of private lots; only time will tell.