Unless he pulls the classic Verzsbicas special it's hard for me to imagine he doesn't run 1:44 and 7:40 at some point in his career, probably sooner rather than later. I am a little worried that he skipped college to go pro immediately, (see: Andrew Hunter) but Hobbs is just so goddamn talented that honestly the sky seems like the limit for this kid. He's got Warhurst training him, not Tinman, I think he's in good hands.
Could he have broken the 2 mile record in HS: maybe? He closed his 8:39 in a 25sec 200m or something insane like that, and he was pacing that whole race off Gavin Sherry anyway, (like a total pvssy) so absolutely could have gone faster. Could he have gone 10 seconds faster? Honestly I think so. His 1500 performances were just so impressive, and he ran 8:39 so easily that it's hard he couldn't have taken 10 more seconds off. But then again, he is much more of a middle distance runner than distance runner. He couldn't even beat Judson Greere at nationals in XC for 5k. That same lack of aerobic ability could skew his 2 mile conversion.
Do I wish he had thrown down an all out 2 mile attempt during his HS career? Of course. But racing rarely, focusing on only one main event is the pro training style that Ron brought him up under. If he had a more generic HS that would have had him race more, with more attempts at different records perhaps he would't have been as fast in the 1500. Just something to think about.