You can condense you whole post into your heart isn’t into it.   I’m little older than you and at least from the row crop side just getting to the point of getting nice iron( can sorta say that with the cows as well).  Calving date can be tweaked if you wanted I’m sure you can find someone to check cows to leave for a bit here and there if your heart is into it.  I farm and work town as well. It can be done if you want to.  

You remind me of my youngest uncle.  In 2019 we had lots of extra forage so he bought cattle and added them to my pasture.   After hauling water and mixing steer feed last winter  his desire has waned.   Cows were fun when Tom did all the chores when he had a portion now so much fun.   He dumped hauling water to the feeders on my wife.  My experience with small scale livestock is a few are enjoyable and therapeutic but more eventually turns to more headaches.