One of the things I'd do over with my Autumn Frontiers campaign is to curtail my instinctual desire to give the players pretty much whatever they want at character creation, within the bounds of the typical "buy what you what with your starting money" setup.
We're now 10 sessions into my campaign, which is set up as a location-based fantasy sandbox and interpreted through Savage Worlds. What I'm seeing is that the players are quite content to use their starting funds ($500 in Savage Worlds) to buy a few really cool bits of gear—and then cling to these items throughout the campaign, forsaking anything else that might come up during their exploration of the wilderness. And it's tough to deny them these pieces of equipment because they're so essential to the players' character concepts. (Example: "I want to play a dark elf who fights with a sickle. Can I buy a sickle?") This concept has backfired because nothing they find out there comes close to being as cool as the neato stuff they bought at character creation. I mean, the sickle-wielding dark elf isn't going to put aside his trademark sickle unless it freakin' breaks apart in his hands.
This is pretty much at odds with classic fantasy campaigning, where characters would encounter new and better equipment, weapons and spells, trading up as they went along to increase their overall potency in the campaign.
Here's another example: Out of an abundance of shared enthusiasm and generosity, I allowed our paladin character to pay a ton of money for a magical sword during character creation. It didn't boast outrageous damage, and it fits really well with his character concept (a paladin serving a flame goddess). It's all well and good—but no other magical sword will ever interest him as much as the one he's carrying right now. After 10 sessions, this character has begun to feel like a toy action figure that was taken out of its box, fully formed and ready to kick ass.
I recognized this during our last session, and I did something about it—I had the ghouls scavenge the paladin's magic sword and his large shield from his paralyzed body during a particularly brutal battle. They ran off with it, and the paladin scourged the lands in search of his special sword, which he found at the session's end.
But I felt lame about the whole affair, like I (the GM) was somehow punishing the player for something. We talked it over afterward, and there were no hard feelings, but still.
Should characters get whatever they can afford at character creation? The answer is probably no, but at the same time it's important for GMs to understand that not every player wants to start off as a bottom-of-the-barrel fighting-man who has to go after goblins with naught but a sharp stick and some lucky dice rolls. Heirloom equipment is fun. How can it be employed to both reward players and keep them excited about venturing forth again and again into the wilderness?
I also think I just need to play up the notion of equipment breaking and degrading over time out in the wilderness. Shields and bucklers don't last forever. If a backpack gets wet, it could ruin stuff stored inside. Chainmail rusts and weakens under repeated blows. Cloaks and robes can mildew and rot in damp weather. And magic swords become instant targets for monsters with more than a shred of intelligence...