Good questions, David.
1) The precise (yet useless) answer is your calorie/maco totals should be enough to help you recover but not so much that you're gaining fat. In fact, you should be losing a pretty good bit of fat. This tells me that if your cal measurements are correct, that you're current level of intake is a bit too high. If you're not gaining weight currently however, you're probably not that far off from where you should be to get the ball rolling, i.e. you would only have to reduce cals a bit to start moving the other direction. That being said, perhaps you might gain a compliance benefit by trying to shift most of your calories later in the day? A lot of people seem to really do well at eating a lighter breakfast and lunch and then getting a pretty big dinner. This, of course, won't allow you to take down ice cream and turn them into abs, but it's one option. If you were my client, I'd have you start with being consistent eating a meat/animal protein at every meal, keeping any non-veggie carb out of the diet unless its before or after training, and cutting back on the milk by a couple glasses a day.
2) Keep doing SS, although you'll probably have to switch over to advanced novice pretty soon. I don't think you should replace a day of SS with conditioning, but on your last session of the week add in some high intensity intervals afterward. You could do these on any type of cardio modality you like (think 20-30s ALL out effort w/ 1:30 rest x 6-10 rounds). Kettlebells may work too. Keep this level of frequency, i.e. 1x a week, for 2 weeks and then think about adding an additional conditioning workout at the end of one of your sessions provided recovery is going well.