The road up to Winfield is in good shape, small potholes and ruts along the way from normal wear. After Winfield, I would say high clearance is your best bet. The road is very rough and full of potholes with water from the recent Monsoon rains. I did not find the obstacle at the beginning of the 4x4 rough section too difficult in a Jeep Wrangler. I took it slow the entire route, as I was in a rental and hiking solo. I parked in the large clearing thinking this was the start of the trail head. The large crater is muddy and filled with water and getting deeper on entry/exit from the rains. I spoke with several folks who made it and they said it wasn't too difficult, but there is no going around it anymore, just straight through.
I took several photos along the way as of 7/29/20. It took me an hour to reach the upper TH from Leadville.