well, i know how you feel. many friends....even though i get them on the right cycle.....still go out drinking and dont' train right nor eat enough protien etc. nothing you can do unless you go live with them and be their personal advisor and beat them with a stick when they do dumb shit.
but for the cycle, here is a how to set it up:
-5 weeks dbol 30-50mg ED (i would say lower dose 30-35mg, but if he is stubborn then......).
-.5 armidex ED during the 5 weeks of dbol (optional, he may want extra water weight/bloat)
-then 5 weeks winny 50mg ED. wouldn't go higher than that.
so i'd run them back to back, 4-5 weeks each. arimidex with the dbol. then do clomid post cycle. its cheap and easy post cycle therapy. i did fine with 5 weeks at 35mg ED dbol. then i did 4 weeks of 50-100mg winny. it was UG stuff, so dosage was a question.
for a beginner i think this is best, you could always go longer on the dbol or winny...but not higher dosage wise.