I think Solomon underestimated the URL scene, because he was blinded by his bodybag against E-Ness and like you said, because other URL rappers were givin' him props even though he hadn't battled on that stage yet. However, it wasn't all his fault. 5 rounds? Whoever authorized this, was an idiot. Two rusty battlers and they wanna spit 5 rounds? fukk outta here.
Yeah, Soul Khan could get any battle he wanted, but if you look at bars they were spittin' 3 years ago to now - he would have a big problem on his hands to adjust.
He probably did underestimate how difficult a URL battle would be. One thing I always hated about Grind Time is how they would film the battles from the waist up, some times even higher. So the battlers never had to worry physically performing their lyrics, or working the stage area. Smack/URL is a different level of performing, guys are expected to move around and sometimes act out their bars. Also when you get on a stage, any issues you have with vocal projection get exposed. Solomon sounds like a spoiled brat sometimes when he projects his voice, Hollow has a similar issue but he works to keep it under control. I think Grind Time did him a disservice with the E-Ness battle, they really gassed his performance when he had a lot of shaky and/or downright corny material. But of course he's one of their idols, they couldn't help but gas his shyt.
Great performers really don't have to adjust to this new style of wordplay. Look at Hitman, Mook, Goodz, Head Ice, Calicoe (at the top of his game), they don't try to keep up with the new styles. Any of these guys can tell you a short story in the middle of a round, and keep your attention. I think Soul Khan fits into this category. He was beating people who were more "lyrical" than him back then, no reason why that would change now.