I'm kind of new to posting pictures on this forum. Are those pictures too big?

Also, I have a few branches that are damaged but still producing leaves. Should I remove them if possible? Even if it makes a big bare spot?

{{gwi:414264}}

IMHO, that last one definitely needs to go. Just taking a wild stab, those super snow storms you had up your way a couple years ago, is the likely culprit. As for the rest, they will likely eventually split themselves, but if they aren't going to fall on anything, then they don't have to be removed immediately. However I would plant replacement trees nearby, and get them to growing for eventual likely failure of the Pin Oaks.

Of course I would be planting the crap out of all that open space too ;-)

Arktrees

Thanks, I will remove that split branch ASAP. In general, I think the pin oaks are in pretty good shape. Do you see a cause for concern or just better to plan ahead?

The tree with the crack down the trunk has been structurally compromised. The outer wound will seal back together, but internally, nothing will change. At the same time, rot may be setting up internally, but even without the rot, the trunk will never be as strong again. Therefore I do think it will eventually fail. When would it fail? Who knows. But likely weather induced at some point. That is why I would get replacements going for when it does fail. I would also plant something other than a Pin Oak for the simple reason if some major disease or pest shows up, then there is a nice uniform row of the same tree to attack.

JMHO
Arktrees

Sounds like good advice. So practically speaking, I could plant a variety of trees at a low cost and then move them to the driveway when necessary at less cost than buying them big?

I would remove any cracked trunked oaks, thenI myself would plant a replacement if there was enough sun for a shade tolerant tree or shade lover.. Or add some Rhodedendrons in the shady gap, or whatever you want. I have planted a White oak acorn under a slowly declining maple, granted it hasn't grown much, but I think the white oak baby will be fine in shade for a couple years, until the maple dies completely.That's my opinion for whatever it's worth.