Melora, I think your post just helps illustrate why the fact that this woman is overweight and her house is messy really should have little to do with what kind of a gift you bring the person. The thing that bothers me the most is not that the OP said that the woman is overweight or that her house is messy, but rather the JUDGEMENTS and ASSUMPTIONS that are made about a person because they are overweight and messy.
Judgement #1: Chocolates are not a good idea because the woman is overweight. She may be trying to diet, or she may not want to gain any more weight than she already has. Well, why are those situations only applicable to her because she is overweight? Isn't that an assumption based on her weight? If the woman was thin, would you take into consideration that perhaps she got that way and stays that way by not eating chocolate? Perhaps she is a diabetic. Perhaps she has an eating disorder. There are a million reasons why chocolates would not make an appropriate gift for a THIN woman, but I highly doubt that if the woman were thin it would have even been mentioned.
Judgement #2: She has a messy house, therefore something like flowers would not be appreciated. Maybe if her house is a mess she might appreciate something bright and beautiful to lighten up her day. It could go either way, but people who are messy have varied reasons for being messy but it's not a single defining feature of who they are. My father is completely anal and my parents' house is always neat as a pin and he hates flowers because they make a mess. I love flowers but would prefer not to have them because my cat knocks them over, spills water all over the place, eats them and then throws up generally all over the one good rug that I have. Flowers may not be such a great gift for ANYONE, regardless of how messy or neat they are, unless you know that they actually enjoy them. The fact that she is messy may have very little to do with how appropriate a gift it is, yet it was presented as a seemingly vital piece of information.
I guess my point is not really that these two things are not facts about this woman, but rather to point out that the world might be a better place if we chose not to define people by their faults but rather by the things they do that make them a good person. It's not a matter of whether she is overweight and messy but rather how important that fact is to someone for whom she is doing many favors. When I think about people who do nice things to me, the first words that pop into my mind have nothing to do with their weight or their housekeeping skills. I guess it's all a matter of perspective.