When your 3 choices are the Cleveland Cavaliers, Milwaukee Bucks, and Philadelphia 76ers, I think most people would prefer to go to Philly. I know I would.
Considering a large portion of your life is spent on the road and you have zero obligation to live in the city you play for during the off season, I don't know how much that factors in.
Philadelphia is a big market and they actually have some heritage. The other 2 are small markets and have no heritage.
Plus I think most would consider Cleveland to have been run horribly in recent years. While Philadelphia and Milwaukee have both kind of "meh," I would say Philly is run better.
Philly has the best cap situation by far as well as the most young talent. Sure Cleveland has the best star in Irving, but a lot of people don't think he'll be sticking around. And again this comes back to how poorly they're run.
Do you think all 3 teams are on equal footing when it comes to being able to attract free agents or ability to go over the cap to fund a contender?
I just think there's multiple basketball reasons why most people would rather go to Philly over the other 2.
But since you touched on the "living" aspect. Do you really think "but you spend most of the time on the road and don't have to live in the region" has ever really swayed a player to a city he didn't want to play in? That's never seemed to work for the small market teams in the past. I'm personally under the impression that most players' spend the majority of their time in the city they play in, but maybe I'm wrong on that.