Free standing is always going to be the most versatile. You can set them up anywhere. But that versatility comes at the cost of weight and bulk. It's probably better to identify your particular needs and choose accordingly. I have no choice but to go with free standing. A lot of folks simply don't need it.
I use both tarps and a 10 x10 free standing canopy (sometimes with attachable sides).
When backpacking/hiking I use a light weight tarp and or tent, (the canopy is too heavy bulky for anything but Jeep camping).
We have used the canopy for backyard cookouts, early spring and late fall (snow) camping gathering place/social room (with a heater and sides) as well as in the pits at stock car races, for shade.
I have been tempted to use it with sides instead of my 9x9 dome tent for weekend jeep camping, and it makes a fair rain sheler/sun shade/gathering place when doing extended (a week or longer) camping, in addition to the 12x12 tent that we use for living.
Fires throw sparks and make holes in close tents and canopies and tarps.
Everyone should own a least one tarp. The ideal size depends on how much weight you want to carry. I think a 10 x 10 ultralight tarp is ideal. You can buy one for about 100 bucks. I've sewn my own, to my specifications. If you have sewing skills, that's even better.
With a tarp, you can make a shelter, use it for a vapor barrier (a protective layer against the cold, against your skin or light wicking layer), a canopy for cooking under, a canopy for a single wall ultralight tent, a ground sheet, a winter canopy for tents thereby extending its snow shedding abilities, a privy curtain. The options are nearly endless.
Use dead falls, rocks attached by bungee cords, or stuff sacks filled with sand to guy out non free standing tents.
I have made several demos on pitching tarps, found at youtube. My basecamp tent weighs 9 pounds, however and is freestanding. Its hard to say what is ideal for any person. Terrain and mobility are key factors when sinking serious money into any shelter.
1. Goretex Bivy Sack & Sleeping Pad - by itself will handle everything from dew to torrential rain
2. Nylon Ripstop Tarp (8x7 up to 10x10 in size) - 3.5 season shelter for almost any terrain or conditions
3. 2-Man Tent - for winter use in snow conditions; optimal enclosed bivouac for one person & gear
My tents have tended to be non free standing, but only required a couple of stakes or a tensioned bungi anchor point. Two hoop, single wall, Goretex, ultralight pocket hotels. Free standing are convenient though. Any tent for winter use needs to be tall enough to sit up inside of and big enough to drag a pack into. Otherwise, what's the point? You might as well just use a tarp shelter.
I always carry #s 1 & 2; during winter I add #3. I've used this system to good effect for several decades.
I used to go tarp (lighter) but after being bit several times by ants etc (we also have nasty spiders and snakes over here in Australia) I have now surrendered and take a free standing tent and suck up the weight.
FWIW i'm convinced ants are going to take over the world.... lol.