In reply to praguepride (msg # 1453):
I can completely sympathize. You want your buddy to succeed, do what he enjoys for a profit, and help them overcome potential pitfalls. Then...they just want to be told they're doing everything right, or want to find criticism with your critiques.
My one time buddy did this once (only he didn't quit his job/s).
Spoiler for what happened to me: (Highlight or hover over the text to view)
It was my birthday, and I invited him over to celebrate by playing a board game. He brought over what he and, apparently, his OTHER buddy were creating. I played it, and it seemed to have steep learning curve, but a lot like Legendary. It's big draw he kept pushing was "The enemy starts with everything they need, and if you don't stop them they WILL win" which meant it was more of memorizing the deck and playing through a precise sequence of motions, rather than making strategy based on a purely random environment. Essentially, the enemy would get sequential bumps to their power, but you KNEW that no matter what you were going to face the same modifier by like turn 15. So I told him I didn't like the game very much, because it felt like many of the turns were spent just letting the villain buff himself, while the players were struggling to just move, even if doing nothing else, to confront the enemy. That it was superfluous what the players did, because if they rushed on, it would take minimum six turns, and they would be severely under-equipped, whereas if they spent some time equipping and some moving, they would likewise be under-equipped, because it would take longer to move, and therefore the enemy would have longer to just equip himself. The only sensible thing to do, was just equip, and ignore the fires going on in the city, wherein you could beat the villain despite the city in shambles, because the villain would come to you.
Well, he didn't like this. Saying "Well my hero has a special card that lets him move" Okay, well why don't you just make ALL heroes do that, and give some other level strategy. "Well, this is an example of choosing the right hero" So after about half an hour of criticizing it, I gave up and asked if we could play something else. To which he said "C'mon, it needs to be playtested. Besides, we only played like five times, you'll do better next time. We haven't even played on the hard mode!" So I had to coolly tell him it was my birthday and we had already played the game five times, and maybe trying something else would be a breath of fresh air. So he just said "okay, I'll just playtest it myself" which meant him playing solo...at my birthday, and we had to tell him we needed to serve the food on the table.
So my experience was far more due to circumstance and who I was dealing with, but nonetheless, it felt like a waste of my time, and was very much unappreciated. So I know how that is. Mike asked how expensive is was to print, and I told him, to which he said "Ookay, I guess I'll just print them out of my bubble printer" and when I told him that would lower the entire bid anyone would pay, he said "No it won't!" to which I just shrugged.
Some people just want to be told they're doing it right, and only have confirmation bias.
Needless to say, because of the exasperation of Mike's attitude, and other things he did that were impolite, Mike and I are no longer buddies.
You don't seem to have extenuating problems, and yeah, probably best not to waste time trying to give criticism if he's more interested in someone else's opinion, evidenced by some of the quotes you shared.