CUFS054 -
Perhaps I am not fully understanding your post but it seems to me that you are attempting to level your TT from left -> right using the stabilizers. It is recommended that you first level your TT from side-to-side using boards or some other means under your tires then stabilize it with your stabilizers. They are not meant to lift the TT but to reduce movement.
I think most people put blocks of varying heights under their stabilizers and the more support and broader base you have in the form of blocks, the less you have to extend the stabilizers.
It seems like you are using the front jack to raise or lower the unit from front to back which is the usual practice.
Under inflated tires? Bad. Top all of them up to the recommended pressure.
More meds? Get a life? We don't dispense medications here or offer psychiatric advice. Against forum policy.
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2008 Cougar 5th Wheel 27RKS
2005 2500 GMC Duramax
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