The reality is that there is seldom a great choice in many places. It's usually choosing between two or more dictators.
When the US supported South Vietnam, it's not that they condoned everything south vietnam did, but had to make a tactical choice between lesser evils.
I guess my takeaway is there is a pragmatic versus idealistic debate here. Ideally America really does want liberal democracies -- if every other nation was a France or Korea, we would be better off.
But there is a pragmatic reality that funding non-free leaders may be a local maximum of stability.