I've seen you allude to something several times, and I'm not trying to criticize your style of gaming, but you really should try to think of the game in broader terms than if it was just a video game. I only mention this based on what I've read from your posts...that's where my assumptions are coming from. Don't get upset with me if I'm totally wrong here
Unless this PC is the kind of guy that would be walking around barefoot (maybe a Barbarian type or something?), why
wouldn't he be wearing boots? Just because he doesn't have magic boots to write in his feet slot on the character sheet? It's odd that the DM would also mention that he is barefoot. Boots are part of normal clothing....normal clothing is part of character creation. I give PCs normal starting clothes for free because; who's running around naked in town besides me on a Friday night of binge drinking? Just because this guy doesn't have
magical boots doesn't mean he must be barefoot. I'm wearing shoes right now and mine aren't magical.
You also mentioned way back about not having anything to spend gold on if you can't buy magic items at the shop. I understand that a lot of players can't wrap their heads around the fact that you can think of a D&D campaign as if it were a real world. I get so much enjoyment out of my characters when I treat them like a real person instead of just buffing them up with better equipment so they are more powerful (like you'd do in a video game). My characters own homes, some owned shops and hired a manager to run it while he's off saving the world, one had a secret hideout that he had custom made in the back of a tavern and paid rent for it. One of the PCs in our game owns a tower and is currently saving money to refurbish it and do construction on it (adding a torture chamber & a guest room for other PCs). I'm sure if you gave a character a goal in life, it would cost money and be something that you can put money towards. Maybe he wants to start a thieves guild or be known as a master wizard that started a mage school...that'll cost money. Maybe he wants to own a large lot of land with a Keep on it so he can eventually retire in peace.
Not everything in the game has to go towards optimizing your PCs power level unless that is the kind of game the DM expects. But from my experience, the most fun and interesting characters were always the ones that had more "life" to them. Anyone can make a He-Man character, not many people seem to make a very interesting character though.
If your group doesn't like that type of game, nothing wrong with that. I just thought it was really weird that you guys would be claiming a guy is barefoot just cause he couldn't buy magical shoes. So I wanted to describe another way of approaching the game in case it may have never been considered.