Re: extraction river plan.
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I'd target his top pair hands for a call here. Since he seems loose, a push has a good chance of being called - it's only a moderate overbet of the pot.
It would have been easier to get it all in on the river if we bet more on the flop.
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In general, yes, but his reasoning for betting smaller is fine. He is more likely to get a call & overcall or a raise because of the "weak" bet. Once one player got out and the other just called him, he could abandon this and bet larger on the turn and river.
I don't think the difference is substantial enough to heavily affect the outcome here. Valueshove indeed.
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