I'm not sure why you took a deposit and offered to refund it if a "last minute change to his schedule occurred" vs saying non-refundable. You gave him an easy opt out and he took it.
At this point just refund the guy and now you hopefully know what to look out for, and require in the future.

At some point you need to tell him to fuck off.

Hang around long enough and you'll learn this.

Pfft. This guy is a clown. Keep the deposit.

Ok well that's different

I'm guessing someone this flakey probably has money issues or makes poor decisions in general, better to just wipe the slate clean and move on.

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OK, with this wrinkle I'd probably give him his "deposit" money back. In general, it's best for everyone to talk through and agree on what the deposit it supposed to mean and the specific circumstances required for it to be refunded. If it's muddled or open to argument, better to just return it.

It seems like he's wasted tons of your time and you're now inviting him to waste more of it. I understand the buyer's having some kind of perverse fun jerking you around, but what are you getting out of it?!? Send him back his money and tell him to lose your number.

Perhaps a buyer rating system is in order?

Well let us know how this works out -- it sounds like this buyer may never have actually completed a purchase, so you could be enjoying the back-and-forth for months to come!

You shouldn't be responsible.

What you should have done is told him to fuck off.

As soon as a buyer starts telling you about his tale of woe, and seven miles of bad road, it's time for YOU to call off the deal, and erase his contact info.

Move on and find a buyer that is serious and excited to put cash on glass.
You don't need this guys problems becoming yours.

My wife has, at least with buying lol

OP - Keep the money and sleep well at night. He jerked you around enough, not to get his money back. Maybe he will learn a valuable lesson this time, and save other people from getting jerked around by this clown in the future.

First id never take a deposit, any sale is done in person in a single transaction. But having said that, id refund the deposti and get the guy out of your life.

Yes he was probably annoying and wasted your time. But its not worth the bad blood or continued interaction with someone who is likely to become angry and seek out soome kind of revenge. In the end the guys flaky behavior didn't actually cost you anything.

This guy could not be more right.
I offer to speak to any potential buyers, and it always put's their mind at ease to then set up a smooth transaction.
And I can usually tell: 'This is someone I do OR do not want to deal with" by the way they talk and the Q's they ask.

Flip side as a buyer:
I insist in speaking with any long distance sellers prior to driving, because you can tell a bunch from a simple conversation, about who you are dealing with and the pin you're interested in.

Tire kickers don't need to be outed/named - chances are most of us already know who they are and how to weed them out.

I don't take deposits, so forgive my question, but why would someone take a deposit if the idea is to just give it back when the deal falls through?

Well you're right, it defeats the whole purpose....but I think $500 is a lot to keep bc some guy wasted your time. My understanding is that the game in question was not publicly listed, so it's hard to say whether or not the wasted time cost any additional sales

It's a good lesson on why you shouldn't hold a game for any reason unless it's a well trusted buyer or it makes sense for you

Agreed. Keeping the deposit will send all the wrong messages. Return the money and make it clear no deal. Period. Deposits are fine but like other said, make sure you feel comfortable with buyer/seller first.

How does one persist after all communication ceases?
Your continued interaction after saying NO is part of the problem. In your case no meant keep pestering me. The perp will do the same thing to the next seller.

Anytime I make an offer on a game that I can't pick up immediately due to distance, I email (and call) the seller and offer to Paypal a $100 or $200 deposit. I ask them to remove the ad, consider it sold, and I'll pick up the game this weekend, and if for any reason I don't take it they keep the deposit.

I've never had someone NOT do it and have never NOT taken the game.

NO means NO.
You can’t complain about the buyer being wishing-washy when you’re being wishy-washy.
When you say no but you mean maybe or yes you’re telling everyone your actions don’t follow your words and it’s ok if theirs don’t either.

You read the part where OP said he lost his job?

No means no for that situation. As the situation changes the answer may change.

Money constraints can change how we respond. If the op was financially comfortable right now I believe that he would be acting differently.

Regardless, keep the deposit. I have given and taken deposits knowing that I could loose it or keep it if they or I back out.