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Ok, here's what I think:
1. Yes, I think plain cupcakes would look great on that stand.
2. It's a toss-up. All white cupcakes would be pretty and very wedding-cake-ish, while white AND pink would highlight the cupcake aspect of it...if that makes sense.
3. I think so. I'd go either damask stand and plain cupcake liners, or plain stand and damask liners.
4. I think plain cupcake lines would look bets with that damask cupcake stand. The damask pattern is very pretty, and detailed enough that a pattern on the cupcake liner might be too busy.
5. I like the pearls, too! Not tacky. Good luck! :)
eitherway, just white or white and pink would look nice. maybe alternate white and pink tiers? i like your liners. check out this etsy seller, the rice paper butterflies are gorgeous and in pink they would look great on otherwise plain white icing:
http://www.etsy.com/listing/54247322/30-edible-simple-elegant-pink?ref=v1_other_2
she also sells pearlized sugar beads that sound like the second option you were describing:
http://www.etsy.com/listing/54247374/2oz-edible-sugar-pearl-beads?ref=v1_other_1
il_430xN_167515291.jpg (16.1 KB, 33 downloads) 1 year old 
I totally second stillme's oppinions/suggestions. Plain cupcakes, especially if they are done nicely, can be very elegant and you don't necessarily need to make them super fancy. I'd pick either the damask stand or damask liners. I think the damask stand with plain liners will look smashing and have a bigger impact.
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Okay, so my man and I are planning on building our own cupcake stand that'll look much like this one:
http://www.ellezdesigns.com/siteimagestorage/projects/cupcakestand/cupcakestand.jpg
My question is, if we have an elaborate cupcake stand like this, would it be ok if our cupcakes were just plain? Like, chocolate cupcakes with white icing? OR chocolate cupcakes with white icing as well as chocolate cupcakes with light pink icing (our colors are black, ivory, and light pink)? I prefer the look of cupcakes with swirled icing like the pink and purple cupcakes below:
http://4.bp.blogspot.com/_MxQWRWfklyE/SX4Wp3yA49I/AAAAAAAAAsY/MBOZ5SCkRgc/s400/Cupcake+icing+kit.jpg
We also have damask baking cups like this (in black):
http://www.bakeitpretty.com/images/large/pemberlymain.jpg
So would having a damask cupcake stand as well as damask liners be overkill? BAH! This stuff is so unnecessarily stressful!
Here are my questions:
1. Would having a cupcake stand like the one pictured above make it "ok" to have plain cupcakes?
2. If yes, should we do just white icing cupcakes or white AND pink icing cupcakes so we can incorporate the color pink into the cake display?
3. If we have a damask cupcake stand, would damask cupcake liners be overkill?
4. If yes, do you have any suggestions on what type of print to use in our cupcake stand aside from damask? We're having a vintage themed wedding so anything with a vintage or antique look will work awesome!
EDIT
I also just came across the photo here:
http://www.flickr.com/photos/diichanjenny/4730231910/#/
and I kind of like the look of the edible pearls on the cupcakes. Would something like that be nice on pink icinged (my new word) cupcakes? And then pink pearls on the white icinged cupcakes? Or does it look tacky?