Okay, some good news from Microsoft this time.
Microsoft and several publishers (EA, Activision, Ubi) have worked out an agreement that if you buy a title on the 360 and then buy the season pass for that title, you will also get that content on the XB1 as well. So if you buy, say, Call of Duty: Ghosts on the 360, and then upgrade later, you won't have to rebuy all that DLC.
In addition, Gamestop (and I presume others will follow) (Aug 19: Yep, Amazon's doing the same deal now) is offering a trade in program where if you buy a copy of certain titles (Like the above mentioned Ghost) on the 360, you can then upgrade to the XB1 version for $10.
For once, this is actually a pretty good idea that should reduce the reluctance to upgrade.