The biggest risk of flying at 1000' AGL (in flat country, at least) with 2000' ceiling is antennas. The new GPS's with terrain and obstacle alerts in their database can greatly reduce the risk of flying into them. Our Aera 500 is wired into the audio panel. It triggered an obstacle alert on an IFR departure a few days ago just as Approach called us with their alarms going off in the background. "Turn right immediately". There is a 1600' antenna just south of the airport. The Obstacle DP says heading 139 until passing 1600' before turning west. Due to strong winds aloft, our ground track was more like 170, bringing up within one mile of the antenna. We were still in VMC, but it still looked pretty close.