Either of my Triumphs would count as the best overall. The '49 had some strange quirks, but it would always get me home somehow.
An honorable mention goes to the '39 HD Flathead and '76 XLCH I had. They were both sturdy, very easy to work on and responded well to engine modifications.
Worst is also a tie, a Honda SL350 was really bad. The electrics were worse than Lucas. I got rid of it when it punched a hole through one of its paper thin pistons. The other was a Vstar that the OL just had to have. I guess that counts as mine because I had to pay for it. It was slower and handled worse than a '50 Buick Dynaflo. When I got a service manual for it and saw how poorly it was designed, it had to go.