I am a Newbie and with the exception of the first few miles of getting used to the lane position and swing taking it home got fairly comfortable quickly. First trip out was another few miles but if you are not comfortable after years I would say you need to drive more.
How about taking it out to a different local spot for lunch every weekend during the "off season". Once you are used to cruising around town with it an open road will be very relaxing. As far as prep goes, do your maintenance and pay for a good roadside assistance program...no worries
I hope you find a solution, life is too short to stress