The time of day will greatly effect the look of the images. The project's location, orientation and weather conditions must also be taken into account. Every project has it's own set of considerations and what looks good can be very subjective. Please take the lighting condition into consideration when determining what time is right for your project.
Sunrise is often optimal for Boston since the sun rises over the water. The sunrise light quality is best seen from 15 minutes before to 30 minutes after sunrise. It typically has less of a golden quality than sunset and the winds tend to be lighter than in evenings. Occasionally there is fog that blows off as the sun rises.
Midday light is often requested when the client prefers the subject to be bright and colorful. It is also harshest light with the most amount of contrast with bright highlights and deep shadows. This lighting condition is often preferred by real estate.
The "golden hour" is highly sought after by photographers and filmmakers for it's beautiful and dramatic quality. When there are clouds in the sky, they often turn bright colors. Looking into the sun will give you sun flares while looking away from it may show some harshly lit sections with deep shadows. This look is best suited for drammatic scenes but may not be the best if you want everything evenly lit.
If you want the city lights along with a dark blue or purple sky, the best time is immediately after sunset during the "blue hour". The drawbacks of twilight shots is that the ISO must be raised in the camera, minimally degrading the image sharpness.
Note: It is only legal to fly a drone 30 minutes after sunset, unless we are flying with a night waiver, which requires pre-approval. For helicopters it is legal any time of day or night.
Cloudy, hazy and overcast days are best for even lighting. It may not be the most exciting looking scene but everything will be lit properly. It also doesn't matter as much what time of day the shoot occurs. These conditions are often preferred by real estate.