When did he look his best? Why?
When did he look his worst? Why?
What do you recommend I do to keep him at his best...or improve him?
July 07 (At previous owners home...I just bought him, pasture ornament for past 5 years):

January 08 (At my barn, maybe 2x per week exercise):

June 08 (Exercising 5x per week):

September 08 (Focus on groundwork, maybe riding 1x per week):

My goal is to really focus on his training starting in Late January 09 (I work retail and I have no time between now and the holidays!) I want to get a plan together so that we can be our best and hopefully really get into showing next season! I may even move barns/trainers. If you think he was at his best in the first photo, please say so and it may encourage me to move!