Yes, I think your plan sounds good. I wanted to add that the skin to skin contact you mentioned is great for BOTH your milk supply as well as bringing out baby's natural inclination to nurse. So, that is definitely an important part of the plan. In the beginning, do the skin to skin without any expectation for baby to latch at all. Just cuddle. When you do try offering the breast, many moms find that it is best to offer when baby isn't too hungry. Some try offering in between regular feedings, a little before a regular feeding time, or after giving a partial feeding from a bottle. Just "experiment" as you said. If baby is getting frustrated, stop and try again later. I recently saw a video of a one month old baby that self-latched during skin to skin contact (it was in the bath tub - nice and relaxing). The baby had never latched prior to that. So, it is possible. You might check out the section of these board for relactation/induced lactation for more advice.