I must admit I was pretty stupid to do Torres del Paine alone with little experience and bad equipment, but hey, I was 19.
I've done it two more times since then, both alone. But one detail worth mentioning is that for famous hikes like TdP, you're rarely alone, there are usually dozens of people doing the same hike, and you end up teaming up with them and hiking together. I'm still good friends with most of the people I met on the trail, especially remote trails.
Is this the type of thing you mean? REI is a brand I've seen so I wasn't aware they did things like that.
I'll be traveling a lot but I'll be hiking/camping alone since I don't have a spouse, so groups would be a great way to make friends and not have as much risk.
That's a good place to start.
My first major hike (9 days at Torres del Paine, solo, I was 19) was hell, shitty gear, overweight backpack and so on, but was amazing and I learned a lot.
It is far easier to hike in groups, there are major gains in weight (stuff for 4 people weigh far less that 4X stuff for 1 person).