You're just terrible at using the Internet if you think it costs anywhere near $300 under any scenario we're talking about here to send $5000 via PayPal. From PayPal's own web site:
Transaction Fees for Domestic Payments
Sending money
It's always free to send money to friends and family when you use your PayPal balance or bank account. Fees apply only if the sender uses a credit or debit card, or if you receive any payment for goods or services. There are also:
No monthly fees to maintain a PayPal account.
No setup fees.
No gateway fees.
No fees for multiple eBay and merchant tools.
Does not apply to Website Payments Pro or Virtual Terminal.
You could also set up a dummy Ebay listing that literally costs pocket change and we could agree to a "Buy it Now" price of $5000 to the winner. Hell, you could send a check for $5000.
If you honestly think anyone here is buying that it's too expensive to send $5000, PayPal or not, you're even more out to lunch than everyone already knows you are. Christ, you can't even man up with a $50+ bet after originally saying you'd do $1000 10 weeks ago, and we all know why my partisan friend.