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One of Cordelia's supports mention Phila's death and that can be unlocked before said character actually dies in the story.Wrong, actually. The fact that he can reach his support with Panne PRIOR to the time skip confirms that Walhart had already conquered part of Valm at the very least before moving across the rest of the continent.
Chrom didn't go to war with Walhart because he took over Valm, he went to war because Valm launched warships toward Regna Ferox, Ylisse's closest ally nation. Virion mentions he went to Ylisse to seek aid, while Cherche stayed behind. It was only after the time skip, when Walhart grew too powerful and started going across the sea, that Cherche arrived to warn Flavia.
The timeline of it all goes something like this:
Pre-Awakening: Walhart starts taking over other Valmese nations surrounding Valm itself, and expands outward. Other nations, like Rosanne, grow worried. Virion plans to offer himself to Walhart to spare his people. His people like him too much and say they'd be willing to go to war over it. Virion launches his final gambit: he flees Rosanne, so that his people view him as a coward and someone not worth fighting for, making them more likely to surrender to Walhart rather than fight and die to him. He heads to Ylisse to recruit allies while Cherche stays behind to keep an eye on Walhart's progress.
Awakening, pre-timeskip: Virion finds Chrom's allies in their first skirmish against the Risen. Virion fights alongside them and starts sowing the necessary seeds for political gains. His supports with Frederick, which can be obtained pre-timeskip, outright confirm that he aims to make political allies.
During the timeskip: Virion, biding time, stays in Ylisse. He can't return to Rosanne lest his gambit be undermined, and he waits until he hears back from Cherche to make his next move, as Walhart did not, presumably, ravage Rosanne yet. Valm is a large continent, and Walhart didn't have ample reason to rush until Validar started ruling Plegia during the skip, as his whole motivation for conquest was to stop the rise of the Grimleal. It makes sense why it took so long. Add to that that Rosanne is decently far south (it's described as fertile, Cherche walked into Wyvern Valley from Rosanne as a child, Wyvern Valley is located in what would have been modern Zofia, and Zofia was a fertile nation, ergo Rosanne is in what was once Zofia). Eventually Walhart takes Rosanne and Cherche flees to Regna Ferox. Valm launches warships toward Regna Ferox's shores.
Post-Timeskip: Virion explains his story and reveals himself as the former Duke of Rosanne, a now fallen nation. He rejoins Chrom after helping to sway him to defeat Walhart. He has now secured aid.
The issue is that your proposed timeline doesn't match up with the game itself.
Supports aren't progress-sensitive, no support is locked until a certain point of the game and it's clear IS writes them parallelly to the story. And this isn't the only time this has happened(example: Arthur's and Elise's convos that mention Arthur having interacted with Xander inbetween them).
There's no dialogue to support the fact that Cherche had initially stayed behind either.
