JDM from ND on 5/12/2022 10:46:52 AM:
Do you want to ride predominantly uphill or down? You could probably leave a car at a local hotel. Deadwood would have many more options. I don't know that there is really any type of lodging in Edgemont. I stand corrected. Google says there are two.
In my mind, your car will be less likely to be messed with in Edgemont due to it's lower population and remoteness. But it would probably be safe in Deadwood too.
However, the hurdle of getting a ride back is difficult. We're talking 95 miles by car. I do not recall a shuttle, but perhaps someone else knows something I don't. Uber? Lyft?
Have you considered breaking the trip up? Do some shorter out and backs on the prettier sections of the trail and just moving lodging accordingly?