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I am having a problem. I am selling an extremely expensive model to a person, but they are demanding to pay when the package arrives at their location I am having some familial issues right now, and I have already driven myself sick with worry over the general state of things. Could I have some advice about untangling this unholy mess?
No money has changed hands at this point, but I'm "stuck in a loop" per say.

In addition, could somebody tell me what is up with people asking for pictures, me sending them, and them never responding to any further PMs?

I don't think I would send something to a complete stranger before they paid for it. He/she might not have the money then your begging to get paid. I would want the funds upfront

What, unheard of, they pay then you ship, no other way around that. Add insurance and pack your model very well of course. They asking for pictures is normal, so send multiple clear images from various angles to their satisfaction.

If they do not pay over a certain amount of time, simply relist the item for sale.

As to the first question check the other guy's reputation (use the search function for their username in post content in the Swap Shop) and you'll see if they've got any positive completed trades (you should see "+1 for [username]" in the Reputable Traders thread), that should give you some additional information. Consider offering to meet them halfway, half the money before shipping and the rest after; if you're going via Paypal (which you should be) the other guy can call it a sale instead of a gift which gives him the ability to yank the money if you don't ship within a reasonable length of time and puts the Paypal authorities in a position to judge fraud. (Remember to keep all the documentation on hand for any package you ship until everything's done with)

As for asking for pictures and then not replying it means they're not interested and a little rude about showing it.

The only time you ship first is when you're dealing with a situation where the rules of the trading forum/community/etc are that the person with the highest feedback ships first.

Does this person have lots of positive feedback.

If you want to go through with it, you should get all their personal information and make them pay for registered mail that must be signed for. Even then you're taking a HUGE risk.

Nope. Never ship anything until it's paid. Pretty much anyone who wants you to ship before payment is just waiting to screw you over.

Write the sale off and move on.

And you seriously might want to consider having a deep conversation with your parents about responsibility. I've seen you mention this before, multiple times, and it's been going on for a while. I'm not sure how old you are, but if you're an adult you should be handling this yourself. If you aren't an adult, then the frequency with which you do this means you should address with your parents how much responsibility you should/do have.

Speaking as someone who has traded with you before, that was a HUGE red flag, and I almost backed out. If one of your past trades hadn't vouched for you, or if you had had any transaction reports opened on you, I would have.

There are ample means to recover your money from a bum deal; it's almost impossible to recover physical goods if the deal goes bust. Money up front or no deal.

Don't send your model. Pay first or bust.

The picture/PM thing, trading online is a tedious process. You literally got to want to do it. Half effort always ends badly, so send the pics, respond to questions, or don't try to trade/sell in the first place.

 Jimsolo wrote:
Write the sale off and move on.

And you seriously might want to consider having a deep conversation with your parents about responsibility. I've seen you mention this before, multiple times, and it's been going on for a while. I'm not sure how old you are, but if you're an adult you should be handling this yourself. If you aren't an adult, then the frequency with which you do this means you should address with your parents how much responsibility you should/do have.

Speaking as someone who has traded with you before, that was a HUGE red flag, and I almost backed out. If one of your past trades hadn't vouched for you, or if you had had any transaction reports opened on you, I would have.

Holy crap, really? I never knew that. Thank you for sticking with me, though. It really meant a lot.
And also, where have I talked about my parents before? They're extremely fair all the time, and I do believe their judgement is correct in this case.

To echo, only send first if they have an AMAZING trade record. Otherwise no deal. Point them to this thread if they don't like it.

Only send after they've paid, no matter their trading record.

You're not a charity.

Always get paid before it leaves your sight.

At a push, send it to a friend who can do the trade in person, but I'd be extremely wary of someone who wants to pay after it's been shipped. The odds are you'll never hear from them again.

Never, ever send anything away without having the money first.

Sale cancelled. Thank you.

You did the right thing. No amount of potential money is worth the stress of begging/collecting/harassing someone.

I'm curious, what was the item?

 Mathieu Raymond wrote:
You did the right thing. No amount of potential money is worth the stress of begging/collecting/harassing someone.

I'm curious, what was the item?

Baneblade.

Never, ever send an item before payment. And cover yourself even when paid, by getting proof of postage, tracking and every bit of attainable proof (photograph of the parcel with their address on it, etc).
If paid through paypal there is nothing stopping a buyer from clicking "Item not received" and janking the money back from you. The process is automatic and holds the funds in limbo until Paypal review the case.
The proof you have will protect you. Without it, you are SOL.

Cash up front.
Always.
Good clear photos of the model before packing and I usually take a photo of the item in the package to show it's well packed.
Always use tracked, insured postage too.
General rule of thumb, if anyone doing a trade doesn't want to pay up front, or doesn't want package tracking, they're trying to rip you off.