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Yeah, other wise the role-play would pretty much start to loose detail over time and that can lead to it to become boring without communication between them.
Basically, there is this day-care that is starting to go out of business because funds aren't coming in to keep the building in check. So the owners of the place have to try and maintain it for a little longer, and the only way to do that is to get rid of some of the pokemon. After a discussion, the two owners of the building decided that they needed to get rid of the pokemon that had "special" needs and had been there for at least over a month. So they decide to give them away to a trainer who actually wants to take care of them unlike their previous trainers.
Once a trainer receives the "special needs" pokemon, he will have to choose between either keeping them in his team, or giving them to another day-care because the one they had just left wouldn't take them back no matter what. After deciding on which of the two choices to do, he will either start a journey on finding another day-care, or a journey that has some "special" things required for things to run smoothly.
Fair enough, you won't really need armor if the Pokemon's life isn't at stake. Probably isn't much of a legitimate market for it, unless you're military/law enforcement.
Seems fair, most trainers won't be fighting super challenging Pokemon. And the stronger Pokemon should still pose a threat, otherwise there's no point.