Love the name Chewie!
You've gotten good advice. As you're regrouping on his freedom, remember that often pups pitch a fit even if you started on day 1. So if you have trouble, don't assume it's because you started later.
My 11 year old Reggie has had the run of the house 24/7 for about 8 years. When we got Coby, baby gates had to go back up. So unfortunately, Reggie no longer has free run of the house anymore unless Coby is crated at the moment. I look forward to a day when we don't have to have baby gates again.
So, I really don't think you'll have that much trouble.