But I think the OP is concerned about the time it would take to retrieve and set up the stroller from gate checking due to tight connections. So, conditional on having to counter-check it, what should the OP do?

I'm sympathetic to the OP's concerns. Generally, the retrieval is fast, but I've been in some places where t's been slow, slow, slow... one time, I was waiting for so long, the pilot himself went down to see where it was...