At the end when you choose your number for the raffle. Do you have to choose the gift card for the sex shop to do the anal scene(s) with Ashley?
No, the gift card is useless for now.
considering dev promised harem at some point - does it mean currently there are no conflicting paths for girls and you can mess with all of them? also - were there any movement in this direction? last time i played was over a year ago and it looked like classic "pick only one or you'll get none" kinda game
No conflicting path but there's an interesting scene in the last update where a phone call with a girl make the MC panic a little bit because he's with another girl at the moment (was kinda funny to be honest). Felt kinda like the beginning of the dev starting to adress the issue and trying to think about how to resolve it.
For now it seems that it would work only by pairs : Roxy-Nikki, Carol-Yuki, Sara-Ashley (maybe Sara-Rachel also). Though there's a special anniversary which shows a harem situation. Seems kinda weird to see some girls together (Roxy and Nikki especially, these two seems more distant from the others as they don't even know the others) but it shows that it still possible to pull it off without being too weird. Apparently there's a threesome in the next update so we'll see how that goes
Anyway, we don't know how that's going to go, but from my point of view the most difficult thing to keep consistancy would be for each girl to accept at least another girl FIRST, then they'll have an easier time accepting other girls afterwards. And the thing is, there's a good angle for at least 5 of them :
they can accept Ashley because MC did things with her to help her get out of the sorority, Carol and Yuki can accept each other because it would resolve their conflict since they could both be with MC and together at the same time, they can accept Sara for the same reason they can accept Ashley : MC help her against the sorority and the bullying, so they naturally grew closer, they can accept Rachel because he helped her with her recent divorce.
Not sure about Roxy and Nikki but these two seems more opened sexually, and once each girl has accepted at least one other girl the rest should be easier to justify.
Anyway it probably all goes down to make them fall in love with you (the 3 red hearts variable situation), have her interact with each other, and then slowly accept that they're other girls.