As cold as it may seem, I would suggest you right this one off. Unless you are one who believes in principal and has money to burn, the cost of you taking him to court is going to be more than $1000. If you do go to court, you won’t win anyway, we never do. The only winners in a court battle are the attorneys. Then again the owner can always say you abandoned the truck, unless you have something in writing stating you were allowed to leave it there. Some owners have a protection built into their owner driver contracts stating the driver who abandons a truck is responsible for cost of the recovery.
As for the 1099 they are issued on or before 01-31 of the New Year. Meaning you work in 05 it is due 01/31/2006.
This is from the IRS site -
When to furnish forms or statements
Generally, you must furnish Forms 1098, 1099, and W-2G information by January 31, 2006. However, you may issue them earlier in some situations, as provided by the regulations. For example, you may furnish Form 1099-INT to the recipient on redemption of U.S. Savings Bonds at the time of redemption. Brokers and barter exchanges may furnish Form 1099-B anytime but not later than January 31, 2006.
Extension
You may request an extension of time to provide the statements to recipients by sending a letter to Enterprise Computing Center—Martinsburg, Information Reporting Program, Attn: Extension of Time Coordinator, 240 Murall Drive, Kearneysville, WV 25430. The letter must include (a) your name, (b) your TIN, (c) your address, (d) type of return, (e) a statement that your extension request is for providing statements to recipients, (f) reason for delay, and (g) the signature of the payer or authorized agent. Your request must be postmarked by the date on which the statements are due to the recipients. If your request for an extension is approved, generally you will be granted a maximum of 30 extra days to furnish the recipient statements. If you are requesting extensions of time to furnish statements for 50 or more recipients, see the TIP on page GEN-7.
I believe the $1000 will be a tax write off. Ask a tax person.