You may be surprised at definition of a free standing tent.
Whether to have a tent that is free standing as defined is of minor importance.
Interesting, isn't it, that the ability to set the tent up on a showroom floor is closely related to the ability to set up the same tent in a city park pavilion, a favorite location for touring cyclists.
Also, the need to stake the tent in wind depends on the severity of the wind. In a 5-10 mph breeze, toss a couple of full panniers in the tent (or one or more touring cyclist(s) in sleeping bags), and no worries.
It's also possible to dry a wet free-standing tent with some clever staking in a breeze. For instance, set the tent up, stake the two down-wind corners, and then flip it onto its top. Dries the bottom as well as the inside. (Bonus points if you attach the fly to the top corners.)
Weight is the only factor I can see in favor of a non-freestanding tent.