A few thoughts here:

re: Chuck D and Ice T(as well as J Prince/Rapalot) wanting to sign VI.
I think it speaks to the business acumen of Chuck D and Ice T as well. They knew that at that time to truly break through they needed a hip hop elvis and they were thinking of who that would be.

re: media hit pieces
Sidebar, it also speaks to how much power the media can have over someone when they aim their power at you. The Dallas Morning News article was a hit piece that may or may not have been justified.

I was around 14-15 at the time, I was hugely into hip hop back then and while I wont lie and say Ice Ice baby was a bad song I think the rest of the album was largely forgettable. Ice Ice Baby definitely captured the vibe going on in music at the time. The sample era was still figuring out the rules and I think the Biz Markie "Thou shalt not steal" ruling had yet to happen...

which brings me to my next point:
Credit to the article for (correctly) pointing out the ridiculousness of 3rd bass using "sledgehammer" to back the track that makes fun of the song using "under pressure". I guess the key difference here is that 3rd bass probably licensed the sample to prevent litigation, but that probably wasnt because 3rd bass thought of that. The labels knew when they needed to clear a sample, I think SBK thought they may be able to get away with it until they sold 10 million copies...

re: appropriation
The article points out that this was one of the first large scale reactions to cultural appropriation. In fairness to Vanilla Ice, he was a young kid that had something huge happen to him so he "trusted" the record label and the marketers to do right by him. They didnt.(and usually dont). Had Vanilla Ice dressed more like he did in the Ice Ice Baby Video he would have caught less flak for sure. MC Search (to me anyway) was the other side of the same coin to me and just as ridiculous. He mimicked the look of a B-Boy just as extremely as Vanilla Ice mimicked MC Hammer. They were both ridiculous, absurd even. Neither one of them were authentic, and I still think MC Search is guilty of it to this day.(seen some interviews, hes mellowed but still...) Also take into consideration how Russel Simmons signed 3rd bass to replace the beastie boys. I think that probably didnt work out how he thought as 3rd bass never really sold huge numbers. Pete Nice never really got too deep in the appropriation, and to me seems like he just was a dude that appreciated the art and tried to contribute. 3rd bass was a label creation as Pete Nice and MC Search werent really friends at all. I think Pete Nice left hip hop to run a sports memorabilia store or something like that.

I think there is a new wave of the same problem (As was mentioned in the article) with people like Post Malone.

Fame is a weird road to navigate, and Im not sure everyone makes it to the other side without some scars. Vanilla Ice certainly has his share. He also has done some boneheaded things, but it seems he may be ok after all. the Vanilla Ice project and holding on to most of his money point to some sort of acumen there. I also think he is finally ok with being "that guy" and owning his ridiculousness. When that happens what other people say cant really get to you. His story could have ended up way differently.