It seems that Jeph is running into the same problem that Willis is - Keeping up with technology when the characters age a lot more slowly than the passage of time IRL. For example, someone on Patreon pointed out that, given what we know about Claire's age, the game console was already a bit of nostalgia technology when she owned it, which makes me wonder if it originally belonged to Aurelia and we have a situation as in Uncharted 4 when young Cassie Drake has inherited her mother's Playstation and copy of Crash Bandicoot.
As for Cindee, I think that poster is probably the QC-verse equivalent to that poster from the 1980s of the tennis player girl. So, probably many teens had that poster and lusted after it! That said... Is Clinton actually pansexual?
Regarding humanoid AI chassis, Jeph keeps on stretching out the timeline to the point where I'm thinking that the first AIs appeared about 20 years before present (around the turn of the millennium if the 'present' is the 2020s). However, because it has been noted in the strip, both the singularity and AI Emancipation Act remain about 3-5 years before present.