There have been several instances where I've had to wait to claim a gate checked bag in poor weather, such as rain or snow. This usually happens on the outbound leg of my trips from ATL into smaller airports where some or all gates use steps instead of a jet way. This combination usually means the poor weather is also later at night when I'm tired and still have a car rental and hotel check-in ahead of me.
For this reason, I've gone to a horizontal laptop/overnight roller (TravelPro Wall Street VIP Deluxe Expanding Computer Brief, replaced by the ExecutiveFirst line) that's large for its class but has never required gate-checking. Unfortunately it's only good for about 2 nights of travel, so longer trips require a 20". I'm considering going to a 20" full-time anyway (likely TravelPro Crew 8 20") but I'm going to see how often the new job puts me in CRJs.