Contango/Backwardation is really persistent. Looking at the auto correlation between M1/M2, if today is in contango/backwardation tomorrow will likely be the same.

This is the relationship between f1-f2 contango and F1 returns. It is obvious (R^2 of .11) that when the curve is in contango, sell vol on the front month.
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Given the current term Structure it is obvious I want to be short vol. On the front month. Where I am looking to improve is, can I buy some "cheaper" risk premium somewhere else? I'm thinking I could buy some Oct with a root time hedge ratio but I doubt that will provide me security if we get a large spike!
From a seasonality perspective buying Oct would be the best bet.
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In that case you are basically making the same directional bet you would if you traded ES futures. Therefore you are not adding anything to your approach using VX futures despite focus on the curve. By simply shorting VX frot month outright you are simply saying ES will keep going higher and front month will converge to VIX.