Honestly in this case a shroud will not help , , shrouds only help when the car is not moving or moving slowly as speed increases the air flow through the rad is fine & the fan is not adding anything , if you go to a larger rad you also have the problem of the small block using a right side lower hose & the big block using left side in most cases unless you use the later model pump housing .
The belt being loose can definatly cause problems it could be slipping under the load & slowing water pump speed so I would fix that first .
When you say timing was set correctly , to what factory spec ? I tend to disconnect or use an allen wrench & limit the vacuum advance curve then set timing at idle around 12* with total around 36* @ 3000 rpm , this alone could be causing overheating while driving , make sure the vacuum advance is connected to port vacuum not manifold , if you are still using it , port vacuum is zero @ idle increasing with RPM , Manifold vacuum is opposite hig @ idle & dropping with rpm , if it is connected wrong that will causing heating also . Adding a spring or even just a coiled coat hanger inside the hose can eliminate the lower hose collapsing