Iniss is WARY at Dean. Dean is unbalanced, as far as he's concerned. But he also lumps him and Sam as a unit and regards them separately as a threat, but unified as an even greater threat. He's also aware that Dean doesn't like Yeerks and it wouldn't be that hard to get Dean to turn on them and try to convince Sam of the same course of action. So he's even more leery. Because Dean is positioned well enough that he could make things really uncomfortable for him.

Tom really likes having a family again, even if it's a weird and dysfunctional and almost accidental one. He likes Dean, he's not as close to him yet as he is with Kaylee and Sam, but he's working on it. He trusts him, which is a big deal for him.