So in the time between the Shire and Mordor, would you say they gained..."experience"? That term seems familiar. I wonder if there might be something in D&D like that.
And that expeirence didn't lead to them learning new magic, or new abilities. It led to them being more mentally toughened.
Which is done for a DnD character by level 1.
Honestly, serious question, when your level 1 players sit down at the tavern, and a mysterious stranger walks up to them and offers them 100 gold to explore the haunted ruins outside of town where they suspect orcs are setting up camp, do they say "Oh no, that sounds dangerous. And scary. We just came for a drink and to have our dinner and go home. I mean, if we found orcs they might kill us. We'd be better off just avoiding that tower and telling someone else about it."
Iirc, they all got something from Bombadil. They got the vial of light (which Sam used on Shelob) and a Mallorn tree seed (later planted in the Shire) in Lothlorien. The point is though they did "accumulate artifacts" and did so in a way remarkably similar to how you would in D&D. (edit: and Sting and the mithril armor weren't just chilling in the Shire the whole time. Bilbo, another halfling protagonist, acquired those artifacts along with the ring on his adventures.)
So... the light which was only useful because the creature in question couldn't stand any bright lights. A tree seed that never mattered until it was brought up again in the epilogue. And that's it.
Sure, Frodo was given Sting and the armor, which Bilbo found. But, I'm curious, did Bilbo end up in a good way by the start of the Fellowship? I remember him being quite distraught and "spread thin" by that point. Almost like the things he gathered on that adventure were bad for his health. Frodo ended up the same way. And we know it was the ring, but notably... Frodo was the one given the armor and sting as well. The other hobbits had basic swords.
Counterpoint, We just had to list out all the magical gear for one the games I'm playing in, because we've been doing Play-by-Post and we realized we'd been forgetting to update. I don't feel like we are getting too much, only a few for each character, but here is the combined list.
Handy Spice Pouch
Alchemical Jug
Bag of Holding
Belt of Transistance
Staff of the Star Field
Cloak of Displacement
Rod of the Pactkeeper +1
Slippers of Spiderclimbing
Magic Maul
Ring of Animal Influence
Pendant of Sophistication
Book of Quests (Plot item)
Escape Crystals (x4)(plot item)
Bag of Beans
Short Sword of Wounding
Chilled Rapier of the White Dragon
Cape of the Montebank
Slippers of Spiderclimb
Magic Cloak
+1 Rapier
Horn of Vallahalla
+2 Magic Great Flail
And at least two more items, people are still checking their lists. And, this isn't unusualy for DnD. Every party member ends up with around 5 or so items at least.
Again, Tolkien's world was very much different from how DnD is played.
Do I think Merry an Pippin serve as the main heroes in LoTR? No. But they are heroic, they are protagonists. Annnnddd..they are just as representative of Hobbit characteristics as Sam and Frodo (and Gollum). (They also noticeably "leveled up" over the course of the books in a way that would parallel D&D leveling up.)
And so you have been talking about halflings' "thematic fit" as a race based on probably the largest individual outliers for that race.
It's silly.
But here is the final bit. Merry, Pippin, Sam, Frodo and Bilbo? They are NOT representative of Hobbits. They are heroes. They are the wierdo's who left the shire. The farmer, the miller, Bilbo's neighbors, the baker. They are representative of Hobbits.
So again, halfling Characters can work fine. Having outliers for the PCs is the point. However, when you zoom out, and you look at the race of people... they are bizarrely out of place. They seemed to have sprung up fully formed into Shires out of the ground and completely seperate from anything else in the world. And for Hobbits, that worked. The idea of these people just minding their business in some quiet corner of the world made sense in LoTR, because the world wasn't that dangerous. There was one source of Evil, it was over there in the East, and it had never really reached the Shire until just now.
But in DnD... that doesn't work. There are too many sources of evil, too many places that evil comes from, and too many forces that have a history of taking and corrupting other races to just ignore halflings.