I hold the stance that man is in a constant state of right standing with God (if he is saved), but that because his mind is not as holy as God's mind is, and has a loooooooong way to go to get to the level of loving that God loves like, that man is also kind of in a constant sin-like state (just that it isn't counted against us), in that we sin all the time but either don't realize it, or aren't able to do better than it until we learn more of God's truths. It's hard to love a certain way on a regular basis unless you actually know how to and understand why you are doing it. Just like playing a video game- maybe you get lucky one time and win, but until you learn the lessons and really know how to play it right, you probably won't consistently win. In the same way, we sin/don't show love like we would ideally be able to until we learn how to do it right. ...Anyway, along that line, I know that a lot of things just take time to learn to get better at, and so there is no reason for me to continually feel guilty about something when I know God is teaching me about it.
That said, I typically only feel actual disappointment in myself if for some reason I know what is right, know how to do it, and I have the full ability to do it, but for some reason I don't (in terms of moral things). But, honestly, a lot of times I realize the reason I did it wasn't because of some blatant "want to go against God" feeling inside me, but often because of fear from what someone might say or how they might act toward me, or maybe because I had a need in my life that wasn't getting met properly like it should have (like if I'm way overworked, or way too incredibly bored with nothing to do, or not being valued by the people around me), and simply knowing that the reason/motivation for me doing something wrong was that a need wasn't getting met makes me feel a lot better, because I know I can prevent future mistakes by asking God to help me get that need met properly.
Anywho, overall, I have very little guilt in my life. Of course, I think I do very few actions that would suggest a need for a guilt feeling, so that is part of it. The other part of it is just realizing that I am a child of God, and as a child of God, that God already knows that I'm going to be making mistakes as I learn, and that it isn't an issue, because basically all children make mistakes as they are learning and growing. It's part of the process (or at least in our imperfect world it currently is).