Check out Chapter 9, Table 1, Notes to Tables (9), on page 617, for conduit fill.
Check out 300.15(C) for sleeving.
334.30 requires NM to be stapled within 12 inches of every cabinet, box or fitting.
I asked for clarification from Jeff Sargent of NFPA at a seminar earlier this year. He stated we should either install a cable clamp at the end of the conduit, or to bush the end and extend the sheathing at least 1/4 inch into the enclosure (box). If we choose the bushed option, the staples need to be within 8 inches of the end of the conduit.