Habitats are risky and not as good as planets imo. It would be trivially simply to sabotage one and kill everyone inside. Just vent atmo into space, poison the air/water, and even a accidental fire could kill everyone who doesnt manage to flee.. Planets not so easy. Some of the same attacks work but u can just walk elsewhere.
plus in a habitat your not really thinking of psychological effects. Its been shown for example that humans needs to see big bodies of water regularly to not get stressed out. So youd need to devote significant space onboard to just that. Plus imagine never seeing the mountains again, or a sunset, or the ocean. The earth is intrinsically linked to our evolution and many of its features are far too big to have on a habitat. I mean not to mention all the microbiomes we interact with unknowingly on earth all the time.
While habitats might be an ok solution for some people there are definitely things we will always need a planet for and imo a planet will always be superior in quality of life.
You could have most people in a relatively small area with the rest for farming.
There would be little need for the equivalent of roads, almost all travel would be walk or bike. The longest distance between two points is less than 34km. If the main settlement is in a ring around the middle of the cylinder, it is less than 17km to any point.