People think it's bad being the tech savy one in the family. Try being the tech savy one AND the artist. Not fun.
A few months ago my Aunt bought a children's consignment shop. (Basically, a store that sells used kids clothes). She asked me to design a logo for her, but that she can't pay me since it's a new business. I was alright with this since she's a good person, and one of the few family members I can stand. I also figured it would be a pretty quick and simple project. Boy was I wrong. She sends me the logo the previous owner had which was literally a crappy stick figure pot with stick figure flowers with smiley faces on them. It was clearly done in MS paint in about five minutes. Everything but the petals of the flowers were black, one set of petals was red and the other blue. My aunt sends it to me with the request "To make a nicer version, but with less colors."

So I go into photoshop and start working on a nice, simple, vector version with one pink flower and one blue flower. Send it to her and what does she say? "Not enough colors! Could you add a few more?" So I color in the pot, the stems, the leaves, etc. Send it to her and: "You know, I don't think I really like the flowers in a pot anymore, can we try something else?" We come up with another logo design which was three tulips in a formation resembling the recycle symbol (she wants the company to be "green"). She really likes it and just has me make a few small changes. I'm all happy thinking were done with it. But no, no, that would be to simple! She decides she doesn't like that one and has me make a whole new one with three shirts of different sizes on a clothes line. I finish that one up and make a few minor changes she asked for. She's happy and I think we're finally done with it since I don't here from her for a couple weeks. Then the other day I get another e-mail from her asking for a black and white version (which I was fine with, and which was easy to do) which was followed with a copy of an e-mail from some lady who my aunt was working with. Apparently the lady was having issues putting the logo up on her site because it wasn't bigger than 300 pixels. Thing is, I made this logo at 300dpi and about ten inches wide and eight inches tall since my aunt wanted a size big enough for shirts. What this lady did wrong is beyond me, but apparently it's still my fault and so my aunt asked me to fix it. I was stumped as to how to do so, since the logo was actually bigger than what was needed so I just gave in and shrunk it down to the dimensions she wanted and sent that and hoped it would fix the issue. I ended the e-mail with the small logo with "I'm sorry, Aunt K, but this is the last work I'm going to be able to do on your logo. I need to concentrate on work I'm getting paid for so I can save up money for an apartment and/or car." She responds with "I always intended to pay you! Just e-mail me how much you want and I'll send you the money. Hope I didn't make you angry."

YOU SAID YOU WEREN'T GOING TO PAY ME! Not that I'm mad about getting paid, but I was working under the assumption I wasn't which is why I said what I did.
Haven't responded to the e-mail yet. Normally I'd charge between $40 and $60 for a logo like I did for her, but I'm tempted to jack up the price now just because of how horrible of a client she has been.

Never working for family again.
My mom now claims my aunt never paid me, but when I had gotten home and asked where my money was she laughed in my face and said she bought food with it. I never been so pissed off. She pisses me off even more now that she denies my aunt ever paying for the job; so I know where you coming from.
Silly aunt. Oh well, at least you're getting paid.