IMHO--I don't use a bridge...some here do for a few weeks.
But if you think his ears are sagging down toward the top of his head (ears not stretched up enough) I'd try to correct that with future posts rather than using a bridge to keep them upright. Otherwise you will risk the dreaded pocket
And stretching his ears straight up as you post should help them stay in a better position and keep the bases from popping out of his ear.
I think MC covered this...but the post goes down in the ear canal, not just in the bell/curved space at the outside bottom of his ear.
Generally you need to wait until teething is done...and go ahead and post a few more weeks AFTER you think they look OK. Better to be safe than sorry.
Let's see what else. 3-5 days each posting depending on how they look...if they get wet, a post pops out of his ear or if they are stinky, you need to look for redness/raw areas and then repost if they look healthy. They may get a little goopy (generally waxy brown stuff), but you don't want oozing nasty smelly crud down in there.
And of course, any time you have problems, or if you're not sure you're actually finished with the posting, you can post pictures here. We're blunt but helpful (I'd like to think) with our advice LOL