Based on all this conjecture, Castform will likely be picked last, given how expensive it will be to get. The easiest to care for and raise would be Vanillite and Snorunt. I'd take either as a starter, and try to immediately get the other.
Next would be Vulpix or Sandshrew. Having hopefully been training Pokémon for a while, I'll have earned some money to pay for the care of them.
Sneasel definitely can't be gotten before Vulpix or Sandshrew, as having one on my team will likely prove too much of a trust barrier for getting them to obey me.
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So that's my catch order plan then. Vanillite, Snorunt, Sandshrew, Vulpix, Sneasel, Castform. And that's only if I'm not leaving the mountain. The other islands have some Ice types too.
Melemele: Seel, Shelder, Smoochum, Delibird
Akala: Eevee, Spheal, Amaura(fossil restoration is expensive)
Poni: Lapras, Rotom
Ula'ula: Crabominable*, Swinub
* Crabrawler is technically everywhere, but only evolves on Mount Lanakila.
Then again, this is all just conjecture. An unactionable plan. I can only start if Looker allows it. Speaking of, its been days, where is he?