Ok... Lots of misc questions here. Hrmm.
Contacts:
Season 5 largely takes place in Chicago. There are a list of Season specific contacts in the Season 5 Prep Files document (See Sticky post here for link) that will be useful, but you will also have the opportunity to earn most of those during the first Missions arc, so they're not necessary to purchase at Chargen. You can buy any contacts you like, but keep in mind that if they're not in Chicago they'll have a more limited use, outside of possible information.
Drones/Gear:
Season 5 Chicago Missions should all take place in and around Chicago. CMPs, on the other hand, are global. Some Missions specify at the beginning that you have all vehicles and drones. Either they were transported or you were provided temporary "copies" to use while on the job (And no, you cannot keep/steal these). In this case, then yes, you have all gear. But if it doesn't say you automatically have them, then it's up to you to deal with that situation in character. Some Missions do stuff like this to challenge the players.

Lifestyles:
Any characters playing in Season 5 should be assumed to live in Chicago, and thus your Lifestyles will be there. You can purchase lifestyles in other cities/locations, but they do not transfer, so they'll be of limited use. But sometimes it might be handy to have a Bolthole in Bogota, you never know. At the very least, the fact that your primary fake SIN gets his mail down there could provide you some cover if the cops end up on your tail
