What is Reddit's opinion of Bert Monroy: Photorealistic Techniques With Photoshop & Illustrator?

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If looking for an Illustrator only solution, and regarding the first image, take a look at Lynda.com courses. Many schools and libraries offer this to their students/members for free. I've also subscribed to Plutralsight and taken courses on Udemy (as well as free YouTube), and in person at our local college and design school; I have found Lynda the best for this type of content.

This drawing is not isometric, but Von Glitscka has a great course on isometric drawings and his process for color combinations and building up his illustrations. This is also another good course on perspective drawing in illustrator. I've watched and done exercises from both of these courses.

Burt Monroy was an early adopter of illustrator for this type of drawing (the first one you included). He shaped out his drawings (e.g. Time Square) in Illustrator and refined them in Photoshop. His book from 2000 is probably still relevant for its process, and he has videos on Lynda.com where he talks about those techniques. He has some great photo compositing courses on the site as well.

However, if you are looking to get a good overall grounding in Illustrator, I could not more highly recommend Deke McClelland's courses. For Illustrator and Photoshop, he has "One-on-one" courses: Intro, Advanced, Mastery. These are fantastic hands on and very practical, and he is probably the best online lecturer I have watched.

As for the second image, that looks like output from 3D software. If you are a student, you can get free access to Maya or 3DS Max from Autodesk for up to 3 years, and you could produce the second image in one of the intro tutorials. The output looks like it might have used a cartoon output type (limited colors, drawn outlines). One face would need a custom UV map; you could instead modify the 3D output in Illustrator or Photoshop afterward. You could also use Blender, which is free. 3D software would also be a great way to output similar to your first image, or at the very least, could create a good template (and guides) for the correct perspective.

Good luck.