Will my boyfriend propose anytime in the near future?

My boyfriend and I have been together almost 3 years (it's our anniversary next month).
We have both been saving for our holiday to Disney World in April. I've never been and it is my dream (which he knows).
He always talks about proposing to me, getting a home together, getting married, then having children.
Currently, we both live at home as we don't have enough money to get a place together. He stays with me at my dads house 3 nights a week. Those nights are the only chance we really get to spend time with each other since he works all day and evening.
I suggested about us moving in at my dads house and he said that he doesn't want to leave home yet, but not long ago, told me that we should get our name on the council list and look for a home.
Going back to proposing, he always talks about doing it, but I'm still waiting. He knows that it would be my dream for him to propose to me at Disney World, but I'm now getting mixed signals from him. He's told me that he won't be able to do it, because of money, but jokingly says 'or am I just saying that to keep it secret?'. So, it's almost like he's hinting towards it.
The problem is, last night, his best mate proposed to his girlfriend (after only a month or so!). I confronted my boyfriend and asked him why his friend could propose so easily and he replied 'well, it's his choice and he loves her'. I understand that's the case, but asked him why he couldn't propose to me. I just got a reply of 'I'm not comfortable with it, yet and I'll do it when I'm ready'.
I understand he's not comfortable with it, but why then constantly tell me about him getting down on one knee and popping the question?
I asked him why, and he said it was because of the past (he got engaged to one of his girlfriends after a few months, but she caused problems and he had to end the relationship).
I don't want to give him an ultimatum and pressure him. But when is it long enough?
I hope he proposes on holiday, but I don't want to get my hopes up.
Will my boyfriend propose anytime in the near future?
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