Personally, no. But my church had a weakness for a time, not having a senior pastor on the scale of years, during which other senior ministers also left. It grew so much anyway, in spite of previous planting efforts, that we needed a new building. That's God at work, we had an organizational weakness which many would say is key, and no charismatic leader, but God brought people in anyway.
Basically if there's a weakness that God clearly works in spite of, that's something we can be free to talk about. With all boasting, we have to be careful with it, because sin is relentless and can turn that into something much worse if we are not careful and if we lean on it too much.
Also, remember the context. The Corinthian church to whom Paul was writing, was hearing criticisms of Paul from others, and they wrote to him when they heard this, and 2 Corinthians is his response back. In this passage, he's turning one of those criticisms on its head.
