Welcome to YT!
Rocky is ADORABLE!
Alot of people free feed and some people don't. It all depends on your preference. I free fed for a while but we have ants (ew!) here that love dog food, so a few months ago I began feeding Jackson a meal in the AM and the PM. (around 9am, then 6pm). He never overate or was overweight when free-fed though so I will go back to doing it when ants are gone.
For little puppies, I would personally prefer to just leave food down whenever they are hungry. I wouldn't worry about over-feeding a puppy as they require much more food than an average adult dog. Maybe wait a few months to put him on a schedule. Some pups are bigger piggies than others though... so maybe just pour the recommended amount of food into the bowl for the day (use a measure cup, the bag of food usually has an amount for puppies).
Good luck!