Wow, that is quite the endeavour! I think your game already has a surprisingly high level of polish for an alleged hobbyist. Having consistent character portraits of this level of quality on top of the work you've already done would be HUGE. Pianofairie also seems like a good choice for this, very cute and charming artstyle, so if you two have a solid enough working relationship to get this much work done then big kudos to both of you. You're both doing a very good so far job in my opinion!
I gotta say that Adam's new portrait makes him look MUCH younger than I thought he was (not sure if intentional or not?), but everything else you showed here looks very good in my eyes.
Very importantly, for all the art I'm showing off here, we've yet to actually get to Bennett, the 200+ portrait variations goliath of a task.
Once again it seems that Bennett is entirely and solely at fault for everything that has ever gone wrong in the universe...
Oh, also, is fifth from the left... Penny? I don't feel like I remember seeing that outfit but the hair and eyes seem to match? Subtle Penny SQ2 teaser? Or maybe I'm just going senile? Either way, looking forward to seeing more!