I have been training angel roll-ups on and off for about 18 months. The bruising at first was very bad, but is less and less each time I return to them. I am in total awe of anyone learning roll-ups in a single month. It took me months to get my first from the ground. I will be happy if I get one roll-up in the air this month after not training them recently. One tip on the roll-down part (which I find way more difficult than the rolling up), as Brandon explained, try to trail the free leg as much as possible to slow the movement down. I’ve found this really helps to prevent whipping around fast which could be bad on the shoulder.