Melissa - I tried that once and mine came out almost doughy and was horrible. I had to actually put it on the cake with my hands! It was that bad. But my recipe has a lot less Crisco/butter than most so I have to measure precisely and get it all right or it's bad news.
What I need to do is figure out how much I should take out of the bag and use the rest. But, haven't done that either! 
It's delivery for me too. I am always afraid of a disaster with the cake on the way. I have a bridal shower to do in a couple weeks. I am making a replica of the bride in her gown as a cake, a 2 tier cake to go along with it, 7 dozen decorated bridal cookies and a few dozen petit fours alll to the same shower. Both cakes are going on top of a cake pedestal. I have to drive 45 minutes. I am just wondering HOW I am going to do this. It's driving me nuts already.
Definitely cleanup!! Cleanup would be my first dreaded part of baking (even though it's at the end, lol). Then it'd have to be waiting to find out how much people enjoyed it. OOOh oooh and because I'm still somewhat of an amateur, it's coloring the icing. I'm ooooh sooo careful as I try my best to get the right hue; in fear that it'll get too dark. ugh...I hate that. But all in all I can't deny the joy I feel when baking and cake decorating.
For some reason I dread making the icing. I hate this part! I guess I'm worried about consistency being just right and I hate measuring all those freakin' cups of powdered sugar. I keep telling myself to pre-measure and put in ziploc bags, but I just never do it.
Invest in an inexpensive kitchen scale. I got a decent one at Target for about 20 dollars. Measure the right amount of powdered sugar for your icing, then weigh it. After that, you won't have to measure any longer--just weight it!
I hate waiting to hear their opinion of the cake when they finally eat it (taste wise). I am always afraid someone is going to bite into a bit of eggshell or worse find a hair, no matter what precautions I take.
I clean as I go and use the icing plugs Newlyweds suggested so that is not a bother and my husband drives while I "protect" the cake and nag him so that is ok. Not for him but for me LOL.
The other thing that bugs me is how I keep fussing with the cake when I'm done. Trying to fix this adjust that, smooth just a little more seems I never quite finish.
The kitchen scale is my most favorite tool! It is easy and cuts my time in half. I also hate the delivery...especially in the summer when tempuratures hit the 100 plus degrees, and even though my air conditioner in my car works great it takes a long time to get it to a nice temp.
DEFINITELY the clean up! I hate housework and dishwashing of any kind...but, I always plan ONE HOUR into my schedule for clean up!
Beth in KY
I try and do the same thing, clean everything before and after, it I dont have all my non-cake stuff put away, I feel I have an even bigger mess afterwards and I hate it.
I was caught once when I was "frazzeled" one morning the kids had made a mess of the whole house, DH was keeping kids away thank goodness, and I was just working in kitchen, had several issues, Powdered Sugar explosions and floppy icing, non-working stuff. Sunday Morning run to health store (allergy cake no soy no dairy no Glutten) and you get the picture. Customer shows up a couple hours early on his way somewhere else. I was mortified. This was the first and it will be the last time, that I dont have at least my stuff in some type of order. It's easier to see and work in, and I dont feel like I am loosing it. I keep my recipes on a clip board along with design and order form, I write my colors on the design and count what I need. I pull out all my tools (all spatula's, bowls and mixing things (for some reason I am always making stuff with at least 6 colors so lots of mixing). So once I have everything there I get started. Cant wait for the day, when I have a kitchen so I can have a place for everything right there and I dont have to carry everything from storage to workspace.
Other than the clean up, I wonder if there is a good chart somewhere that could say how much icing you need approximately per square inch (I dont want to reinvent the wheel). I always make more colored icing, but then I have leftovers of little stuff, I get the kids to use it when friends come or I make cupcake and decorate for Daycare, but maybe there is a better way. I wont be able to give out cakes to daycare for ever. 
Delivery also bugs me, I have learned a lot from a fallen cake. Best learning experience is a having a bad one! 
Sorry I got a bit off topic.
Good Luck. 
Melissa... I just dump the bag of sugar too. I make either a half batch, which is one bag or a whole, which is two for bigger or multiple cakes. i don't measure it out.
the worst part for me is also the waiting to hear all was okay.... I never feel right until I know the cake didn't taste terrible or fall over, etc.. or like someone else said find something "foreign" in it or something. LOL
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