Question: I understand why players who are in "lose now, win later" mode would stick with the game--the prospect of something better down the road. But why would someone playing a "win now, lose later" character stick with the game once they got to the "lose later" section?
Whoever posted that original comment can clarify what was meant, but I see potential confusion here with the pioneering D&D game.
A key point here was pretty common to the early RPGs. The expected mode of play was like today's RPGA "Living Forgotten Realms" in terms of a large pool of people forming ad hoc parties for specific adventures, and having "stables" of characters of various levels (and, in old D&D, henchmen and hirelings possibly including monsters).
It was not expected to be a game of finite duration, either, with some final finish line to cross as a "winner" or "loser".
So, a character could retire from adventuring without the player retiring from the game.
Originally, a Hobbit was limited to attaining 4th level (Hero) as a Fighter. It made sense to retire that character, bringing it back into action only when there was some incentive. Defense of the Shire might be a reason, or a quest for some special treasure. One such treasure might be a means (such as a Wish) allowing the character to exceed the normal level limit!
The Hobbit's special advantages could keep it a viable contributor to parties averaging a couple of levels higher, or more with magic. Indeed, it could be more than a match for a 6th-level Fighter (the Dwarf's limit) after the latter had taken some hits.
Moreover, a 4th-level Hobbit was quite powerful relative to a 1st-level
anything!
Finally, the advantages of gaining levels -- even for magicians -- were mostly to do with the kinds of activities mainly yielded more levels. See the circle? Raid and pillage the underworld, and you get better at ... raiding and pillaging the underworld.
There were other things one could do, and most people doing them were 0-level normal men. There was no rigid "skills system" limiting characters to being only so good at Diplomacy or possessing only so much Knowledge.
It did not matter very much whether an individual Hero was the 120th or 536th best Fighter in the world. In either case, he or she was probably better than more than 99% of the soldiers in any army -- able to beat several at once, and more in succession.
Above all, that was a character who dared what ordinary people would not, who went where they could not with any hope of returning, and possessed thereby both wealth and personal power. Just how much of the latter depended greatly on
charisma, which was
not a "dump stat" to canny players!
The Hobbit could have powerful henchmen, hire mercenaries, build a stronghold, and cut a domain from the wilderness -- so becoming truly a Lord or Lady in the socio-political scheme, as opposed to the scheme of experience-level titles.
When "you and what army?" has an answer, attitudes sometimes come in for adjustment.
There can be much less "power-seeking" undertakings, as well, when a character's game shifts to concerns having less to do with levels.
None of that prevented a player from
also having at last gotten a Magic-user to the eminent station of Wizard. That was a different kind of game, a very dangerous one. M-us were sort of like Old West gunslingers.