Just roleplay becoming a millionaire - a problem with Storyteller Backgrounds

Recently our group had a discussion about the progression of earning new dots in Backgrounds in an Old World of Darkness campaign we've been playing. He's been trying to beef up security in his Dragon Nest (magical lair from EvWoD), bolster his Resources by robbing some ATMs and strengthen the bonds with his demonic advisor. But because all of these interactions have been rather subtle, neither the GM nor other players noticed this until it was brought up recently that these things haven't budged on his character sheet. Unlike everything else that can be bought with XP, this one part of the character sheet falls under "just roleplay it out and GM should award you some points", which falls under the unguided realm of "mother may I" which doesn't ever seem to be a good part of an RPG. Let's go over the problem in more detail.

Hey GM, is this enough for Resources 2?

What are Backgrounds?

Backgrounds, also sometimes called Merits, are parts of the character in the Storytelling System that are mostly extrinsic to the character. They are things like income, fame, people that work for you, how influential you are in the region, how powerful of a mentor is guiding you, etc. Unlike D&D, in the Storytelling System your character can start being a rich, influential political figure if you spend your points right, which can be pretty fun.

The problem is that in some of the Storytelling Systems, like Vampire the Masquerade after character creation raising existing or getting new Backgrounds cannot be done with XP, unlike everything else. Instead, they are raised as a consequence of the narrative and roleplaying.

While this isn't universal (Chronicles of Darkness let you buy any Merit with XP and Exalted lets you buy some Merits with XP), it can certainly be annoying.

Just roleplay it out!

I personally dislike any system that tells the players or the GM to just roleplay any broad part of the game out without any guidelines or rules. They always leave things wishy-washy and even if the GM wants to be conductive to the players advancing their things, it often feels arbitrary. How do you gaige of a player has sufficiently roleplayed becoming a millionaire to raise their income? How do you balance one player nagging the GM consistently to get those Backgrounds they want vs a player that is less forward about what they want? Should a player that can make money out of thin air just be given the money Background another player invested a good part of their starting character points into? If a player wants to roleplay getting some powerful artefact as a Background, should they just be allowed to? How do you roleplay learning Mandarin for five years if the in-game sessions happen day-to-day?

This is kind of like when character's social influence is left entirely to roleplay - the option is never as useful as the concrete option of violence. If you have the XP to up your proficiency in a skill like Melee, you as the player are in control of the character getting more competent and that has a tangible application on the session - your numbers go up, you are numerically better. You can't rely on having that same agency if your GM doesn't facilitate you getting the Backgrounds you want (even leaving aside some more hostile GMs that don't want you to get them, even well meaning GMs may forget to set the scene you need or you may fumble meeting a potential Mentor / Contact / Ally, etc.).

Just spend the XP!

Seeing how the New World of Darkness solved this issue in 2004, I'm surprised this approach hasn't been backported to the 20th anniversary edition in 2011. Just letting the players spend XP to buy points in Backgrounds would address this issue and give players the agency to push for their character improving things external to themselves. As always, you'd want to also tie the system into Sanctity of Merits (a system from Chronicles of Darkness where if you lose something you spent XP on, you get refunded that XP) not to make players lose their investments and feel bad about it.

Of course, one can argue whether or not some particular Backgrounds (such as Mentor, money, artefacts, etc.) should cost XP if sometimes players can happen upon them, but that's a bigger topic for another day...