Trained by hall of famer John Hawkes in partnership with his sons, Wayne and Michael, All Too Hard is set to begin his autumn campaign in the first group one race of the year, the A$400,000 ($495,000) CF Orr Stakes (1400m) at Caulfield on Saturday.
The Orr has attracted 11 entries, including King Mufhasa, Mawingo, Pinwheel, Wall Street and Callanish.
Boss rode against All Too Hard in a jump-out trial at Flemington last Friday and was impressed with the colt's development over summer.
"The way All Too Hard looked the other day in that trial, he has matured into a magnificent colt," Boss said.
"He has grown tall and athletic which is a great sign for the horse's connections. What he did the other day, they way he went into the barriers, jumped cleanly, cruised along nice and relaxed, then gave a very good kick was just outstanding."
Hawkes has also nominated All Too Hard for the A$200,000 Expressway Stakes (1200m) at Warwick Farm on Saturday in case of wet weather in Melbourne.
Boss, runaway leader in the Melbourne jockeys' premiership, said he was also taken by the Gai Waterhouse-trained Proisir.
"Proisir won the Spring Stakes at Newcastle and ended up contesting a Cox Plate, running competitively, and all in his first preparation.
"I can't ever remember a horse doing what he did last spring. He has a lot of talent; he could be anything."