RE: Ill. Non residence deer Licences
If your friend is leasing ground and then selling hunts he must have an outfitter's license.
There had been some rumor about transferrable 'outfitter' and 'landowner' tags, but that does not appear to be the case. These tags as proposed would have cost about twice the current rate.
There is legislation pending to do away with the NR cap, and I expect that will be the case.
Good luck!