Like the OP, I'm officially an old geezer. Our driveway is roughly the same size with 2 LARGE turn-around/parking areas. Trees and some embankments lie on both sides of the driveway for 600+ feet. There are 2 hills, somewhat steep, but short in length. Crushed stone.
Contracting the work out is indeed easiest and cheapest.
Getting quality work in a timely manner can be challenging. Once found, hang on to that contractor! Waiting for a plow contractor to show up so an ambulance can access your home is not a viable option. Have a back up plan.
To me, I use the snow and leaf removal as a good excuse to buy "toys". For snow removal I use a cabbed tractor with (with heat!) and a 6' wide FRONT mount blower. My back and neck would never tolerate a rear mount. I did the open station gig for 15+ years. Cabs rule! Until the driveway freezes up and has a bit of a snow base, I leave some snow to pack down.
I just changed our leaf removal approach. For 20ish years will used a contractor. He did good work, and was priced fairly, When he showed up! A replacement contractor asked for crazy money so...more toys!
We have a loader mounted, 40 HP (yes, 40!) blower. It will blow 90% plus of our leaves well into the woods. The remaining we used a lawn mower with bags.
If having a tractor and the associated equipment will be a fun hobby for you, go for it! I love it. If it is a necessary evil/work for you, contract it out.