I have been having problems with my boss wasting my time with meaningless assignments that don't have all the details necessary to complete.
It's not a waste of time to your boss and it's an opportunity to gain his trust to work on more challenging assignments.
If the task lacks details then ask questions, write down more details and learn how to work on your own with little direction. Before you approach him to ask more questions make sure you're prepared a list beforehand. So that you can gather more details with fewer interruptions of his time.
I also have problems with my boss telling me (every time I try to suggest proper planning) that "This is just the way things are"
It sounds like you're telling your boss how to do his job. Instead make a list of your recommendations in writing. Write the recommendations in a positive tone, be creative and acknowledge that you don't know everything. If possible, ask a coworker to review your list and ask for feedback before you forward it to your boss.
When someone says "this is the way things are done" it means that this is standard practice for the company. This could be related to the culture of the business. You shouldn't take this personally. It's not about you. He might agree with everything you say, but be completely powerless to change it. He might not tell you that he agrees. He's been there for a very long time. You should trust him. He knows how things work there. He understands the politics of it all.
I have already gone to my boss's boss and we may have a meeting later today to discuss my boss and I's interactions, however, I'm not 100% sure about this.
I'm not 100% sure about it either.
This might not go well for you. Be prepared to make an apology, but above all talk less and listen. Avoid speaking about your boss. Speak only of the process, the tasks and the planning. Say nothing negative and offer positive ideas and solutions. If you can't do that, sit and be quiet.
I'm not telling you to ignore the problems, or to feel defeated. I'm telling you that this particular meeting isn't the right time to make any demands or complaints about your boss.
Take a break from the problems. Give it a week or two to calm down. Come back this website and ask questions about how to better assert yourself with a difficult boss. Be specific about which issues you have. Take each problem one at a time and in a while things will improve.