Shadowrun 5 is in progress, and the end is in sight.
I need to clear up a few mistaken assumptions;
The SR5 files started with the SR4 files. We did not re-invent the wheel.
The majority of the changes between 4th and 5th (from the point of view of the data files) have been to the details of how things are handled. There are relatively few changes in the data itself. For example, in 4th, you can only have one specialty/skill - spending karma to get a new specialty replaces the existing one. In 5th, you can get an unlimited number of specialties/skill (but only one at character creation). The list of skill specialties barely changed. That means that there's very little room for a contractor to help - the majority of the changes that needed to be made were to the way skill specialties functioned, not the list of skill specialties out there.
For things like the gear, most of them changed their description text and cost, but relatively few items were deleted from the gear list, and relatively few new things were created, and very few changed the way they actually functioned. That also makes it hard to make efficient use of a contractor, because the way Hero Lab's editor works, the contractors couldn't edit the raw data - I'd need to take in what they created, inspect it all for correctness, and then replace the existing material with the new versions, and then change the Ids of the items back to what they had been, rather than the Id created for the new version. The amount of time I need to spend on all that is barely smaller than the time it takes me to make the 4th->5th changes myself.
We will be using contractors for Run & Gun and all the future Shadowrun 5 material.