Welcome Matt, cb500 is an excellent bike one of my favorites, the 450 is a legend, both worthy of rebuild. The 350 was a surprisingly nimble little machine that is often overlooked as a collectable and decent riding machine too. Your grand dad had good taste.
I rebuilt my first 350 when I was 17, the rebuild was straight forward and easy even for a beginner with some tools, the 500 is just like that only it has 2 more cylinders. just have to follow the manuals. The 450 is a little bit different and most people have trouble with the cam chain when rebuilding but otherwise the rest of these bikes are very similar .the 450 and 500 share many of the same parts.
Will you be doing the work on the 500 or will the Honda shop be doing the work? It has been my experience that an unexplainable bond will form when you work on the machine that will aide both rider and machine in years to come.