Mmmmm 
So… Agatha Holmes it is then.
I grew up and still live in the city. For me, it’s the exact opposite. I just love it when I could be somewhere without lights, though even here in the Chicago area, I find suburbia pretty lit up (though not as much as the city.) It wasn’t until I was 18, visiting my cousins outside of Hobart, Tasmania, Australia, that I looked up in the sky and realized why it was called the Milky Way galaxy. It was truly awe-inspiring. I love that feeling. Also, the quiet. Here, no matter where you are in the city, at any time of night or day, if you’re outside there is background noise. I’m very much used to it (especially living near an airport under the flight path), but when I am somewhere where there truly are no manmade sounds in the background, it’s a beautiful feeling.
I love it too! I love the country, and I love looking at stars. What I don’t like is dark houses staring at me.
Is anyone else familiar with an area such as the OP complains about? I’m wondering how much lighting he expects in such areas.
I took the darkness for granted when I was young. My family lived in the country, and we could see the stars. The Milky Way is pretty darn amazing. Now there’s so much light pollution that you can barely even see any stars there. And now I have the bad fortune to live in a place where I can’t see much of the night sky. I never get to see all of the cool stuff like meteor showers and the aurora borealis. 
I guess my neighborhood is a candidate. We all turn off our outdoor lights at night unless we are expecting guests or a delivery.
My question is if the OP is approaching homes where he is expected by the occupants. If he is expected why is he venting on a message board instead of to the people he apparently knows? If he’s not expected? Well, tripping over something in the dark isn’t the worst thing that can happen to him.
And there are no street lights? And the street signs are not reflective?
Where (in general terms) is your neighborhood? Like “a suburb of 20k 10 miles outside of a city of 300k.” I just ask because I’m trying to figure out which of the many neighborhoods and suburbs around me (Chicago area) would fit the bill. And as far as I can tell, the bigger the house, the more folk around here seem to want to light it up at night.
With GPS today, I wouldn’t think it as important to have individual homes and their addresses lit up to find them.
I personally still find GPS will say “you’ve arrived” when I’m still well short or possibly even past the address I’ve programmed. It should be accurate enough to tell me, but I often find myself looking for addresses anyway, and this is in daylight.
Several times a year, I have people turn up here whose GPS sent them up the wrong road entirely.
Yes, there are street lights and reflective signs. But the OP was mostly complaining about the lack of lighting on the properties. You know, the ones owned by bougie assholes who make life so tough on uninvited guests.
I couldn’t say(for sure) if the OP is a troll or not, but look at how he’s stirred up shit and pitted (no pun intended) us against one another, simply by bringing the socio-economic into it. Everyone is already (understandably) defensive and now we have two false categories: “rich assholes and their darkened bougie streets”, and “visitors who suck if they complain, and aren’t welcome anyway”.
I shall now amend my response to: I hate when residential streets have poor lighting. I am a frequent visitor to one such neighborhood and it’s always a challenge for me.
Get shoe lights. Amazon has them for many types of shoes.
I have Croc headlights.
Don’t walk out much at night anymore unless the dogs tarry their last potty break. I may step out on the deck.
Or hey, a good flashlight. Always easy to use.
Seriously you are in more danger from cars that don’t see you. Wear reflective stuff if you’re gonna stroll neighborhoods in the starlight often.
Apologies, guys. It wasn’t entirely clear to me exactly WHAT the OP was complaining about.
To the extent he complains about finding a particular address and finding his way to the front door, I guess I’m curious about whether he is an invited guest, a delivery person, or what. I’m still trying to figure out which of the 100s of neighborhoods and suburbs around CHicago might fit his description.
Why are you cruising unknown neighborhoods at night? I was invited to a party just this past Saturday night in Westchester, and it was well lit because they were expecting guests who didn’t know the area, so I’m thinking no one expected any guests from different locales that particular evening in the area you were “visiting”.
My guess from the get-go is that this is somebody doing deliveries of some type or otherwise involved in a house-call type of industry. I’ve heard complaints before about the suburbs and exurbs where you can’t find an address because it’s so dark, but never quite phrased as in the OP. I don’t think this is a particularly rare gripe.
I don’t know what would qualify in the Chicago area. There’s definitely places I’ve been to where I’ve had difficulty finding the address because the house address itself wasn’t well-lit (or sometimes even locatable), but not really where you had to use your brights to drive through the neighborhood to see anything. There’s generally street lights everywhere. Maybe out in unincorporated parts of the suburbs you may get this.
Poorly displayed addresses has long been an issue - and not only in “dark bourguosie” neighborhoods. I often thought the practice of painting addresses on curbs, or reflective signs near the street where there are no curbs, is a good idea. Our address is in maybe 6" tall numbers, above our garage door facing the street, directly under a downward-facing farm-style light. I figure if people don’t post their address prominently, they must not care if their invitees have trouble finding them.
I guess I don’t go a ton of places that I am not familiar with. A week or so ago I went to an open house in Oak Park (neither particularly dark nor bourgie.) I googled the address and saw the house is on the east side of the street, the 2d house south from the intersection on the E side of the street. Was able to get there no problem (tho it was during the day, the same system would have worked at night. Would have also worked somewhere like Oak Brook or Burr Ridge - wealthier areas with homes more spread out. Or - as you say - some unincorporated - tho not wealthy - areas near me in DuPage. But even in relatively congested areas in daylight, I have had to stop, back up, scan addresses to find my destination.
I’m not sure the OP has described a vocation other than gambling. Doing so might help understand his gripe.
Why?
Serious question. Are you often trying to find unfamiliar places in such neighborhoods from a car, and the street signs and numbers aren’t easy to read? In which case, it’s not necessary to light the whole street; just the numbers and signs.
Or are you walking, and having trouble seeing where to put your feet? In which case, why not carry a flashlight, instead of wanting the whole street lit? – bicycles have headlights, too.
This. Please do. Without it, you’re a lot harder to see from a car in the dark, or even in the dim, than a lot of people realize. \
Maybe he was delivering pizza…?
Really? You can’t possibly fathom how driving down an unlit street could be challenging? You may not share that problem but I don’t think it’s hard to imagine.