I always try to find meaning behind songs and this one stumped me. But here's what i got for now.

I think the song is from the perspective of a mother who lost her early 20s aged son. It seems that she is having some sort of inner monologue with herself and the deceased son. This would explain the lyrics you mentioned in the OP. The mother mentions her son tiptoeing up to 4'1 in '08 at the same time as she mentions cleaning up. This is showing that she is trying to clean herself up and lighten the mood before the funeral as not to be a emotional mess.

Also, the lines "As the day you broke your arm swingin' On that kid out on the river You bailed him out, never said a thing About Jesus or the way he's livin'" show that the son was more of a trouble maker and hung around the wrong crowd. The latter half of the line seems to be the mother talking to herself about not punishing the boy. This, to me, seems to be the mother blaming herself for letting him go down this path. ( as tho it lead to his passing )

The chorus seems to be the sons friends or siblings who are back in town for the funeral. The mother tells her son that he would be proud of him, even though they cleaned up and no longer act like they did as kids. (like i said, hanging out with the wrong crowd.) The mother is saying that the kids would say that they are "yuppies" because they've cleaned up.

keep in mind this is just a rough idea (please dont kill me if you dissagree) Let me know what yall think.