No one expected four freshman to be picked in the first round. I know Calipari and his staff didn't. John Wall was a no-brainer but even Demarcus and his mother were told he needed a lot of work and to mature if he wanted to make it. There were zero expectations in terms of draft status in regards to Eric and Daniel coming in. Daniel's decision came even more out of left field and there was a lot of family stuff going on that I'm not comfortable with sharing but he was encouraged to explore his options like the others.
Doron Lamb, Stacey Poole and Eloy Vargas are three players who will be around 2-4 years in the program unless they exceed those expectations. I question if Knight will go after one year because of the value his family places on education but if he's projected lottery they're not going to hold him back. Kanter's too good to stay and Jones is an enigma. He's got all the tools the NBA covets but is he a 3 or a 4? You're going to have a deep pool of talent with Poole, Lamb, Miller, Liggins, Polson, Vargas and Hood with the possibility of either Jones or Knight returning to go along with Gilchrist, Teague and Davis and whoever else gets added.* Of course you can never predict these things with 100% accuracy because you're dealing with so many different factors in play.
As to your second point:
I think people are hypocritical, petty and prone to extremism when it comes to sports. I've got some insight into the Memphis Basketball program in the Calipari era as well due to a relative who worked closely with the Men's Basketball Program and the Grizzlies via a Corporate Partner. Never heard anything that didn't go on at every other major program (and yes there were probably several things that towed the line like the car thing but even Tubby Smith lets that stuff slide because it's so hard to prove.) with the exception of one: Strangely, a handful of extremely well paying internships seem to always fall into the hands of basketball each summer. I've heard the NCAA looked into it and said "fine" but I've never confirmed that. Really not that shocking as that type of stuff goes on everywhere.
And yes, I do think he can win a championship with his recruiting strategy. He wants to recruit the best of the best. He's just going to need a more complete team than he had his first year. As talented as they were, as fun as they were to watch, they still had some holes that just couldn't be filled and a lot of them showed in the WVU game.
*and that's a whole different conversation and what's pissing off a lot of Calipari's non-friends in the coaching fraternity.