Thanks everyone for their input. I really, really appreciate it. I'm going to stop wasting everyone's time at this point, and redo the boards with carrier board footprints, just for proof of concept. I'm thinking place the holes over the pads, fill the hole with paste, iron needle tip in, and go?
@Buriedcode, you recommended using a wire. I'm not sure how that would work with surface mount pads. I'm afraid if the wire would be filling the hole, it would prevent the solder from making it down to the pad and having a good connection.
@Artag, Yes, I was planning on using the through hole variety where the plans would normally call for side-mount LED's to try to make the POC easier. Unfortunately, in the above case, I can't use them in this spot because there's components on the other side.
@Blueskull, that is very kind of you to offer your soldering skills.
@Jeremy, I've seen the Dotstars. So more reliable on the data end and smoother animations?
@Mr. Scram, I would happily pay $1 a piece for something reliable. : )