1 Corinthians 16:6

And it may be that I will abide, yea, and winter with you, that ye may bring me on my journey whithersoever I go (KJV)

Then: Paul hopes to be there and stay awhile, perhaps through the winter before leaving again. Possibly he's not sure which churches will next need his presence because he indicates his plans after that are not yet formed. Baker (p. 243) brings up Romans 15:24 where Paul voices desire to head to Spain.

Now: Churches spend a lot of time looking ahead, finding ways to grow their individual ministries by working with local and foreign missions. Planning is always an integral part of church growth.

Extra Source: Cornerstone Biblical Commentary 1 Corinthians (William Baker), 2 Corinthians (Ralph Martin & Carl Toney), ed. by Philip Comfort. Carol Stream: Tyndale House Publishers, c2006.