Yes, years ago I use to be one of those rent a cops who worked in private and public buildings.
Some of you need to realize that are a few guards who aren't even aware the laws regarding jurisdiction but generally most do. Since I've done this for a while (especially highrises) let me give you the do's and don'ts that may be helpful. I too have gone out and photographed photos of highrises but keep some of these measures in mind.
1. If you know someone who lives and works in the building ask them to invite you that way you are authorized by them to be on the property. Depending on the scope of the property rules you may want ask before walking around the property with a camera. Private property building managers are the one's who oversee the property rules being enforced by security and it's usually a building governing board or corporate who makes them. It would be best to be accompanied by the person who is hosting your visit on the property. Never walk off on your own without authorization or the host because most security offices can monitor your were abouts and will confront you. Unless it was authorized by property management or hosting resident I wouldn't do it.
2. The public sidewalks, parks, street, squares, parking garages and lots are your best friends. If you're approached by security just tell them you're just a tourist taking photos and that you are standing in public right of way. (it's what I usually tell them) Usually, most of them will leave since they may already know the rules but just wanted to check to see what you were up anyway. If they are gung ho and give you a hard time just simply walk away from them since you are not on their property. They can't do nothing to you.
If they say they will call the cops then you may want to contact them as well
to question the guard's jurisdiction. Most cops should know about public right of way vs private. What can they do unless they have you on camera for trespassing or doing something unlawful.
3. You may want a camera with good zoom if you want get a close up.
4. Remember most of these places have cameras so be careful by not doing something stupid like climbing over a fence to cut through the property to take photos from a public sidewalk on the other side. Not good...they will either confront you or just simply dispatch the police for suspicious activity. Just walk around the property.
5. Don't argue with them or say something threatening. All the reason to call the cops even if you were standing on a public right of way. Some cities and towns can have very strict soliciting and loitering laws that could get you picked up by the cops because you appeared to be loitering and making threatening statements. I've seen this before. (usually with homeless). Just ignore them and keep taking your photos. Don't give them any ammo. When the cops get there just tell them you were just walking though taking photos from a public sidewalk and minding you're business.
6. Keep in mind that every city has different ordinances so you may want to learn about them first. What works in NYC may not work in another city or town.
Hope this helps