Just a couple of thoughts. If I'm reading this right, you have winny taken every 3 days. The half life is 9 hours. I would want to take it every day, oil based, water based or oral.
Even if you have used insulin before, I would start low, 4iu and make sure you are getting 10g carbs per 1iu that you inject. Post workout is ok. Personally, I prefer preworkout, taken 30 min before training, 30 min after my last food intake, which contains the carbs to cover my insulin spike. I also will then consume a carb shake intra workout. Be sure you do not go to bed before the insulin has finished working and carry fast acting sugar with you at all times, in case you go hypo