As for tickets, the only Authorized Ticket Reseller (ATR) in the US is CoSport. If you see tickets / packages from anyone else, they are not authorized ticket sellers but selling tickets on the secondary market. CoSport sells individual tickets as well as hotel / ticket /hospitality packages (but they do not do air). If money is no object, one of their packages is the way to go as they have great availability for their packages. To show you a comparison of the costs, CoSport has a "flex" package that is 5 days 4 nights. Cost is $9,000 per person based on double occupancy. For that $18,000 you are getting about $2,000 worth of tickets. So you are paying about $16,000 for 4 nights in a hotel. You can go on booking.com or other reputable sights and get private apartments in prime locations for about $600 per night or less (a total of about $2,500). So you are paying CoSport a $13,000 plus premium. But you do avoid the hassle of trying to find the tickets that you want. Only you can tell if it is worth the price.
We have been to the Vancouver, London and Sochi Olympics and yes at times it has been a hassle getting what we want........but in the end it was well worth it.