I don't think the mere act of expecting better or more, as the case may be, is bad. So far, it seems to me things have an unnerving habit of turning out how we expect they will. From what I've seen, people who don't expect to amount to much typically don't. People who expect things to go badly for them are often right.

So personally, I expect a lot.
But. I also hold myself to that "a lot" standard. I don't expect things to come to me without effort or kick. I give a lot, I make a lot of effort. But I do also expect things that might appear big or quite "out there" for others. I think you need both. Both to give it your best, and to expect best. Or at least, as you said, better.

That's for entitlement.
As for waiting for better moment, better health, etc. to take care of what needs it, I think there's mostly just now. Better things could come, but so could worse. How long can you afford to wait in the hope that "better" is the right bet?