Hmm, well, I think it looks fine.
I don't know about running a cycle for longer than 8 weeks for your first one. I think by week 8, you are, or should be, mentally and physically fatigued trying to keep up with the training, diet, etc.
I don't understand how deca is sooooo bad. I think this looks like a mild cycle, one with minimal chance of sides. Sure, there is the chance that the deca will give him some progesterone related sides, but at 400mg/week, that should be very, very low chance.
And the eq won't aromatize at that low dose, either, so estrogen sides are out.
Could this cycle be 'better'? Sure, but then most can. Winny is expensive, and will he really need it for this cycle? I doubt it. Could he add test? Sure, but I sure as hell wouldn't put him on 500mg/week. Now that is asking for sides. Water, estrogen, etc. If he adds test, it should only be like 250mg/week. Other cycles he can up the test. On this one, it would only add expense, and little to no benefit to start it at 500mg.
Sure, if he starts to experience deca-dick, pop some test. But many people have done a deca/eq only stack and had excellent results.
I think he will keep most of what he gains as long as he does the clomid therapy correctly.