I understand getting annoyed at the same old never ending story, but....
I was born with an over sized empathizer (that I managed to tame a little over the years) .... The thing is, after living this long, I know that getting that lovely outfit or two (or whatever), would only have a momentary joy and then, the rest of someone's life is still the same, so it doesn't really make life better like you dream it could. You can't tell folks though, because you want to leave them their dream.
I try to make a mental list of other subjects I could try to steer things too, questions I could ask. It doesn't always work, but I try. I hate to totally give someone up just for being annoying, although I have. Sometimes their world is just so small. I can't imagine being a young mother with a disabled child.... alone.
As for the trip and would I do it? I probably would once if it was something I was deeply interested in.(reading reviews of course, for any unhappy surprises others experienced) Like you, I would look to see the one that I thought would be the greatest interest to me and I would plan it and do it. We need a few exciting things in our life on rare occasion.
Your dahlias are beautiful!