I'm on my 5th grill and 3rd Weber propane, and still have all 3 Webers in operation.
I found an old gas grill in the woods behind the house I rented in college. Shelled it out, added a MASSIVE piece of countertop around it (I worked for a cabinet company at the time), and probably made 1000+ burgers on that sucker in 3-4 years. I loved charcoal because of the smell and taste. Then the wife's dad wanted a new grill, so I inherited his old Weber. A few years later, he wanted a smaller one, so I inherited his second Weber, and gave the first one to my parents. That was 15+ years ago. It has had 1 set of grates, and my parents still use it on a weekly basis, even though it is 20+ years old. When we built our new house, I wanted a larger grill, so I sent weber #2 to my parents place in the mountains, and it cooked me some great burgers this past weekend. It is 15+ years old, but still looks like new when you knock the pollen off of it. Living outside, uncovered. As a replacement, I bought a used Weber Platinum on craigslist, and it has been great. All that to say, you get what you pay for with a Weber. (or you get what your father in law paid for?
) Somewhere along the line, I got a cheap stainless propane 4 burner grill that a friend was giving away, like a Char Broil or something. Didn't cook as evenly, and didn't hold heat as well. Got the job done, but I gave it to someone else because it was too finicky and didn't cook as well.
Nothing to add on the wood pellet side, but after cooking on charcoal so much in college, it was weird going to a propane grill, because the meat tasted so "clean". I imagine pellets are a nice balance between the lack of flavor from propane, and the sometimes overwhelming charcoal flavor.
For me, the biggest thing is time. I can be cooking on my propane grill in 3-4 minutes. I don't smoke stuff or cook things for hours, so if I'm doing burgers/steak/chicken, its usually a 10-20 minute process, and I don't have to spend any time or thought prepping things. Keep a 2 tank rotation and it's always ready to rock.