To orient this in my mind, please tell me who owns the driveway in your pics, you or the neighbor?

It's a private driveway, shared by us and 3 more owners.

A pair of matching urns or large vases or something like that, one on each of the gateway pillars. Seasonal flowers in the urns would be nice. Right now, all those pillars look alike, which is confusing.

Finding the path to the door was made difficult by the routing and blocking off a more easily accessible path. I think you're going to need to make the gate entrance more obvious. A way to do it that comes to mind is to make some kind of roof structure. That makes it larger, more visible and important looking. so that it's the first entrance upon arrival.

Should we increase the height of the gate entrance door? And add more green to make it more curb appealing?

You could add a little more height to the brick piers to signify that they are the terminal points of the line of fence. The gates themselves, I would simply reverse so that their tallest side is the one that connected to the pier and their shortest sides abutted one another when closed. The gates don't need to be heightened because they are low security (Fido can't get out) ... not to keep fence-jumping criminals out.

We do like the idea of raising the height of the gate entrance door, or adding a roof-like structure like Yardvaark mentioned. This will make it more of a noticeable entrance. Antoher thing that will draw people to the entrance and add curb appeal would be a water feature like a tiered fountain. One would look really pretty on the inside of the gate and next to the steps. This would add a really welcoming sound as people come up to your house. The one we have shown in the mockups for example purposes is the Acanthus Two Tier Fountain, but a birdbath or bubbler would also be really pretty surrounded by more greenery.

I agree with @User's comment: "A pair of matching urns or large vases or something like that, one on each of the gateway pillars. Seasonal flowers in the urns would be nice."

I think using planters on top of the gateway pillars would be very classy and add instant curb appeal.

Here are a couple you might like to consider; the Longwood Fluted Urn Garden Planter or the Moreland Urn Garden Planter.

You can view more urn options here.

Thanks so much. Shall I go with something a bit taller? What kind of plant will go well over there?