What are people doing about roads/driveways that are there but marked Private Way and/or are gated/posted No Trespassing? Sometimes it seems fine to run them anyway in my area; other times it seems like I’m gambling with the wrong end of a shotgun or unwanted Dobie-o-Matic encounter.
normally I donot trespass 
In the new maps there are fewer of thes occasions luckily.
Don’t trespass. If it’s marked private, it’s not for us.
Also, I should not be importing private roads to begin with. The Overpass Street Query that I’m working with ignores them, and a few other types of road.
If you spot a private road in CityStrides, you can fix it up in https://www.openstreetmap.org 
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Thanks. To clarify, I don’t trespass when it’s marked No Trespassing. Ever. What I’m wondering about specifically are roads that on-the-ground are marked with regular road signs that have an extra “Private” tag on them, or somehow are marked as Private Way (there’s a LOT of these where I grew up on Mount Desert Island in Maine). James, I’m starting up an OpenStreetMap account to try to address some of the ones around here in western MA. No idea how to do it yet, but wish me luck tagging them as access=private!
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There are a few people in this forum that are very skilled with OSM - feel free to post questions in #general if you’re ever stuck with something.
There’s also an OpenStreetMap Chat if you have/use Slack. Our channel alone isn’t worth the effort (yet?) but the rest of that workspace is full of really helpful people. That group can probably help you decide how to handle all these “sorta private” streets.
Yeah, i LOVE manipulating OSM and make it more and more the real life copy of the world. So if timezones permit, you can give me a heads up to start mapping. After a few tries it wil come easy. Especially tagging existing objects
In some cases “private” means for cars but not for pedestrians. In my opinion “no trespassing” means no pedestrians.