Intelligent, considered answers, thanks. I would recommend some more lessons with a good instructor, perhaps down in Biscayne Bay where the boat will travel along with you after you get up on your board. It is amazing at how fast you can progress removing waves, the need to stop due to approaching shoreline, bystanders, etc.. The wind may even be a bit stronger out there as well. A few hours out there could equal much more time working from shore in unsheltered waters.
If you have a traction kite, I would recommend regularly practicing emergency depowering with it along with PM to make sure it works. In most severe accidents, the rider never seems to bother or at least activate it successfully. You want to practice it often enough imaging likely scenarios to improve the odds of fast success.
As you are working on basic skills currently, I would recommend practice self rescue. You don't need a lot of wind as a rule and you would be best not experiencing this for the first time when you actually do it in need. The same could be said about body dragging upwind. It is fairly easy but only if you practice it a bit.
Regarding weather planning, launch selection and emergency scenarios it is best if these are adequately treated in your course. Sometimes this happens and sometimes not in these early days of organized instruction. There is a fair amount of information about these subjects on this website including:
http://fksa.org/forumdisplay.php?f=12 ,
http://fksa.org/forumdisplay.php?f=29
At 275 lbs. you have some special challenges in our lighter winds. I would say you should find a good flat kite on the order of 16 m in area and a larger twin tip. I would not start with a traditional C kite at this point. I have had good luck with the Underground FL-XXXL board, not sure if it is still available but it is a nice light wind board. When the wind is light you may not be able to get out as often say as a guy around 150 lbs. particularly while you are still developing kite and board skills. If you have a fair amount of time wakeboarding already you may not need to consider this. If not, at a heavier weight I think you might benefit with some time at Quiet Waters Cable Park. Often the greatest barrier to learning to water start on a board is inadequate wind power. The cable park may bypass this issue while you cultivate board and edging skills independent of wind needs.
There is a lot more to know about kiting than you can gain from either trainer kite flight or body dragging. So, I would say hook up with the best instructor you can find in a good setting. Talk about what you want to achieve and what is a reasonable time frame to do this in. More ideas about selecting an instructor at:
http://fksa.org/showthread.php?t=656
Good luck and let us know how you are fairing.