tobster911,
I agree with B2N2, good advice. Make your buddy an I/R rated pilot who can file an IFR flight plan so you can legally go into cloud - that way you're legal and safe if wings level turns into anything but!
Also, someone before mentioned using Flight Simulator. I couldn't agree more. Back when I did my IFR ticket, I used MS Flight Simulator for the basics: getting my "scan" going, beacon bashing with and without wind, basic ILS work, etc. The beauty thing about this is that you can set a place in space and time and change the conditions - start out a 5,000' heading north to a beacon in IMC and fly over the beacon. Then go back to your starting point and add a 30* crosswind at 10 knots. See how things change. Do it again with a 60* crosswind at 10 knots. Then 90* @ 10. Then up the wind - 15 knots, 20 knots, 30 knots, etc. See what corrections you have to make to stay on track.
It is a great way to see the theoretical aspects play out in a nice, easy "practical" setting where the only thing getting hurt is your heat sink and the only thing you're paying is the electric company.