Cal: Yes! Looking forward to this whenever it suits. :)
Tes: Honestly with as long as she has worked at the shop I feel like she'd be one of his closest friends just by proximity and mutual love of books, whether she wanted to or not, but she's fun so he's not bitter about it.
For what it's worth I imagine when she was in charge his mother would have scolded Tess for having upcharged Cloves who could afford it, but Finn'd have slipped 'round behind her like "They can afford it, and it'll offset when we undercharge the folks who we know can't - it's fine. Just keep track so the numbers work out at the end of the week." - and to be fair probably does the same because if someone comes in trying to decide between two books (because they can only afford one) he'd be like "Oh, we haven't put the signs up yet but we're doing a half-price book thing today. What do you know? You don't have to choose. What luck!" and then would just dock his own pay for the difference if he couldn't make it up another way. (But hey, if a few Cloves could even things out - all the better.)
100% here for all the setups and wing woman escapades. Shop dynamics first because priorities, but I feel like as long as she pays attention and can spot anyone sizing him up all she'd really need to do would play 'hype (wo)man' effectively unless his would-be target had a friend she'd need to distract or entertain. I feel like these would be fun, non-serious threads and I am here for it.
Btw, if she asked he definitely would be up for teaching her the press, but I also think it'd be difficult for him because no one has learned it since he did and the last one to teach it was his father, who was teaching him immediately before/as he was dying. ...I would expect a fair number of "smoke breaks" where he goes outside to be alone and cry for a minute. ...LIKE A PROFESSIONAL. (Side note: If he started teaching her he'd def. make sure that if something happened to him the shop would go to Tess rather than back to his mother, who without him definitely shouldn't be handling the shop. ...I'm imagining he'd know who Tess's sister is and so he wouldn't be likely to tell Tess about the will adjustments out of concern he'd suddenly come down with a terrible case of 'beaten to death in an alley', (joking! mostly!) but I think her wanting to know would cement for him that she actually cares about the shop/books as a business so he'd feel good about it. ...Not so good about it that he'd tell his mother about the decision (again, he's not trying to end up dead in a ditch), but good about it on a personal level.)
-- I have to start work/be a functional adult now, but I'm definitely curious about Lukas and the others. When I get a break will review the bios I haven't read yet that you mentioned and come back with THOUGHTS.