Worried about his anger issues...

My boyfriend and I are thinking of taking a holiday. It’s the first time we will be on our own in another city, and I am a little worried because he has these temper tantrums that can ruin our trip completely. He says he has his anger under control, but we have had numerous bad dates because of his inability to stay calm. I am nervous because I will be alone and can’t leave if he loses his temper. I am also definitely going to do this because I will get a better understanding of what he’s like when we’re alone, and that will help me decide if this is a relationship worth pursuing. Am I being too cynical? Should I just give him time to understand me better, or find a way of dealing with his temper?
You shouldn’t have to work your way around someone else’s shortcomings, specifically because they are the ones who need to do the work. If he knows he has a problem and doesn’t do anything to fix it, you are only condemning yourself to a pattern of repeated behaviour. It is not cynical to see what someone is like before choosing to go on with a relationship. That is exactly why people spend time together to understand each other better before deciding to commit to something more permanent. Tell him why this is important and what is at stake and give him a chance to try harder.

I want to date someone who is unreachable because of the difference in our economic statuses. Should I go ahead and tell them how I feel at the risk of disappointing myself, or wait until I am in a better financial position?
Why assume the person is going to evaluate you from the same financial lens you apply to yourself? If you have feelings for someone and know them well enough to have that conversation, you should do so. If they reject you, accept that decision and their reasons, and just move on.