Harrison vs. Simon should be a solid indicator of Harrison's level. As much as I love Simon and draw comparisons to Murray, he doesn't seem to be able to be more solid than he already is. Top 10-15 range seems to be his comfort zone and he's susceptible to normal losses again top 30 players. This is a match Ryan should be able to take. It'll test his consistency and patience, and his aggression and how well he balances those two because he'll need to do just that. And controlled aggression is where the game's at now.
if he plays a close match but loses, he's just showing good forward progress. If he doesn't even play a close match.. well, he needs time, he's no prodigy.