The question then is why should someone in a city not be equally able to maintain their gear, especially when according to the lifestyle rules, someone in a city is apparently LESS able to construct a secure shelter and therefore more reliant on their armaments?
I think they can, if they put in the effort to learn. It's a matter of necessity. A woodsman
has to have those skills, because no one else is around. Living in the city? It's easy enough to get someone specialized to do it for you.
It's like anything else. How many people living in the city know how to can their own food? Or replace their own roof? Or do moderate maintenance on their cars? Heck, or even cook a real meal? Living in the city now, I can tell you not many. Now ask that question about the country people and that number goes way up. Everyone I knew growing up on a farm knew those things. It's not that city people don't have the intelligence or capability to do it, they just don't need to do it, so those skills go unused and a specialist usually does all of those things. I know this is purely anecdotal, but having spent half my life out in the country, and half my life in the city, it seems city people spend WAY more time playing video games, on the internet, and watching TV than country people do. But it's not because they are lazier or whatever. It's because most city jobs are 8-10 hours a day and you're done so you have that time. Growing up on a farm, you worked 12-14 hours a day, so you didn't have as much time. Lord knows now that I'm a software analyst in the suburbs, I have a lot more time than when I was back on the farm. Ironically, I spend most of that free time working on my garden lol.
Also, I can tell you from first hand experience that living out in the middle of nowhere you have this attitude of taking care of your gear like your life depends on it, because sometimes it does. Compare to the city, where it's easy enough to just drive down to ACE hardware and get a new one. So by simple matter of necessity, preventative maintenance is critical for the woodsman.