Question: How did the phone booths, the trolley, and the vending machines end up in the digiworld?
Question: Why didn't Beth or Josh report Jacob to the faculty for everything he was doing in terms of bothering Beth? Jacob tells Josh to back off because Beth is "spoken for", he tries to win Beth at EL's party, but gets ignored by EL after Josh can't outbid him anymore, so Josh ends up winning, and he even tries to get Josh expelled from Ithaca University by pretending to be his Ancient Philosophy teacher and telling him that he can take his exam at a later date when Josh phones him from a payphone whilst on the road trip to Austin.
Answer: It's funnier if Jacob constantly bothers the characters and gets away with it, and receives his comeuppance in the end in an over the top manner (he forms a suicide cult but is the only member that actually kills himself).
Answer: This happened in the TV show. We are never told as to how they got there but in the last episode Gennai asks them if they could return the streetcar to San Francisco for him. So my guess is that people like Gennai left the items there.