You cannot get another OPT for the same level of degree (in this case your 2nd Masters).Since you are alrady counted on the H1B cap in 2009, you wont have to worry about the quota. If you used 1 yr in H1, then you have 5 more yrs remaining. The total yrs in H1b will still be 6 yrs, so any time you used up will be decreased. You will get your next h1b for 3 yrs and 2 yrs after that if you have used up 1 yr of H1b in 09. The process for applying H1b is the same as you did before except that you just would not be subject to the quotas. This is from my personal knowledge. Please correct me if I am wrong.