1. I have a good ultra-light hiking tent that I'm happy with but it's not free standing. I've the impression that free standing is preferable so that when camping in places with a picnic shelter, for example, it's common to set up your tent inside the shelter. I plan to camp whenever possible. So, do most use free standing? If not, are you happy with your stake-requiring setup or, if you had to do things over, would you opt for free standing?
On my first tour I used a Eureka Spitfire Solo, it’s not freestanding and I didn’t have any issues with it. There was one or two times I couldn’t stake it in the ground so instead I used the cordage for tie downs and tied each end to a solid object nearby. I now have a Nemo Hornet which is freestanding but I only ditched the Eureka because the Nemo is lighter.
I'll mention that the Spitfire is especially well suited to staking out with limited anchors. One at each end does it in a pinch since you don't need the fly held out tight when under a roof. Some tents require more anchor points just to stand. Usually that is manageable, but take it into consideration for the tent you have. In a pavillion or gazebo there can be support poles, picnic tables, or you can run cords off the edges of the floor to the surrounding dirt. Still if you have a tent that requires a lot of anchors just to stand it may be a hassle.