Making Puerto Rico and Washington DC states has been suggested as a way to screw the Republicans, since (it seems to be assumed) they would both be reliably Democratic. I don't really understand what the idea of DC not being a state was supposed to achieve, so I can see that. And PR seems to regularly get shafted as things stand, so I can see statehood as a way to fix that.
For the flag? Only Americans care about such things.