What I took from his comments was that he wants us to cheer him on and buy new equipment...
He said repeatedly that he wasn't gear shopping. Couldn't be any more clear than that. He just wanted the opinion of folks who he obviously respected in this field. That opinion would aid in his determination of whether or not he would get some replacement gear. So, the advice you kept stuffing down his throat was EXACTLY what he was trying to avoid and the antithesis of his post.
I made several suggestions and recommendations. I also asked to see more of his work to properly critique, but apparently that is not what he wanted to hear.
Which he repeatedly said he wasn't looking for. You weren't comprehending the words he was typing that stated he wasn't looking for gear and he wasn't interested in getting gear recommendations.
So I gave honest critique based on the samples provided.
You gave a childish response because he didn't want to hear what you wanted to keep pushing at him since he'd already said he wasn't interested in buying gear quite yet, and you insisted on recommending it.
For instance, compare the pp on photo 1 (dog) to that of photo 3 (flower). Can you explain how someone who went through that much trouble to pp the flower to that extreme, failed to do something as simple as mask the effect from the dog's eyes?
Yup; he said his computer crashed and he just had a few photos left; who knows what state they were in. Frankly, photography (at least the art of CAPTURING the image) has nothing to do with how well you work in photoshop. In fact, if you require that much photoshop skill to MAKE a decent image, you're probably not a very good photographer. Might be time to take a little self-evaluation here.
I'm no pro, but c'mon. I'd probably change my opinion after seeing more of his work.
Why? If you think you'd probably change your opinion after seeing more, then you shouldn't have made such a sweeping and negative statement earlier. Statements like the one you made are careless and hurtful without any foundation. It doesn't speak very well of your character. Sure, it's more difficult to encourage people, but I suppose that's kind of the point, isn't it? Feel free to take the easy way at other people's feelings; sabotaging their ambitions is a nice side-bonus, eh?
To answer his original question: "Just wondering if I should move forward and buy some new gear."
The answer would be no. For the time being learn to use what you have until you have reached its maximum potential, and the equipment is limiting you. Clearly, it is not.
*sigh* again, he said he sold his gear and was thinking about getting replacement gear. Using what he has got means a good dose of imagination. How about you evaluate the images in his head? Of course, they'd probably be unworthy images to you too. BTW, what exactly qualifies you to determine a good image? I'm curious. Published? Taken some art classes? Taught any art classes? Given any photography classes? I'm curious.
To the OP: You know what you paid for the advice you solicited; I would submit that at least some of it is worth exactly that