she complained once when I changed plans with her and it cost her $5.00
and
We were going to take her into the city for a $1000.00 dinner this summer.. I will never do that now..
Wanted to do so many nice things for her
One thing that occurs to me is that you may not be seeing the spending of money in a similar way. For example I think the hotel room is $365, the nice thing you planned to do for her is $1000. What you cancelled on her was $5. It is a huge gap in disappointment caused, if measured by the cost to the wallet. $1365 and $5.
Does she value things done together in a similar manner? People attach value in various ways. For example, Spexy once calculated how much money he had spent on our relationship. The amount as it tallied over the years was jaw dropping. Not surprisingly, given that a massive chunk of it was just flights between two cities. He had also spent a lot of money buying things for my son and me. He picked up part of my son's hospital bill for an emergency surgery. Other things I coveted and he purchased for me because I would enjoy them. Yet, I think offhand, if he were to be asked how much he spent on our relationship, he would at best have a rough figure - even though he had calculated in detail, checking his bank account sheets. My situation is even worse. I'd be off by a hundred thousand dollars, easy.
What did I spend on him? Next to nothing compared with him. I don't remember that amount either. But I made handmade chocolates and soaps for him, gave him things he found uniquely useful and so did he. I'm not as attracted by the very expensive flights (that made our relationship possible!) as I will always remember when he bought me everything on a wish list I had. I was reminded of us by the $1365 and $5 gap.
Perhaps your girlfriend doesn't understand the value of the things she is refusing in your perception? Or perhaps you are offering her a different kind of value from what matters to her?
One possibility is to discuss with her what she finds special about a gift or a treat, and if her expectations are less about money, you could make plans for being with her that address what she enjoys in a gift or treat and maybe aren't so expensive so that you don't feel the disappointment as badly if she is not able to follow through.
People are different. When we got engaged, I told Spexy not to bother with a ring because it would be wasted on me and he already spends a lot just to be able to be with us often enough. His mother already had a ring to give me, which is a different matter, but if she didn't have, Spexy wouldn't buy one and I most certainly wouldn't even notice. What is an engagement without a ring? Imagine. For us? Fun. Who cares about a ring? Now I have one and it is sitting on my finger and doing nothing particularly useful. Do I not value a diamond ring? Truthfully? It is ok. It isn't a big deal, but I wear it because Spexy put it on me. I have no idea what it costs.