Are you having trouble getting to your maintenance level now? And yeah, like Rukas said, you want to be at least 500 calories above it (for losing weight, you go for least 500 calories below it).
You should drink the protein shake right after your work out (as soon as possible). If it's okay on your stomach you can mix your protein powder with Cecemel chocolate milk. The reason why you want to drink it right after is to help your muscles recover.
Best thing to do is to eat 4-6 times a day. I'd advice you to look around for a bit. Look for carb-protein-fat ratio, what/when/where/how to eat (or maybe just the what/when), and what food has a high amount of protein (+ low/high carbs, so you have some wiggle room with carbs). It's much easier to process all the information and actually put it into use when you do it yourself. Especially since you have to find a diet that works for you.