Sounds like your client "forgot" to tell you...

that this is a PITA.  And now you will probably need to pay someone (maybe a few someones) to get you a clear title.

And don't forget that there is a use tax on the title transfer that you'll need to pay as well.  And since this will be a traceable transaction...you may want to make sure that you report the "income" on your personal return...and Yep...that'll fun you more money.

Suggestion for next time...have him pay in cash.  Looks like this one COST you money!

Pretty sure this can only be resolved by Judge Judy!

1. You need to find out if said Leon holder is bankrupt or OUt of Business.
A. Bankrupt- harder, but information Act allows you to contact state to negotiate lien for pennies on dollar.
B. Out of business - need to find controlling business owner and have Leon lifted.

I recommend consulting an attorney "friend" for help on form letters. I'd they do it, your talking 4 digits.

2. IDK circumstances for the barter however you are assuming a lot of responsibility. Perhaps you could re-barter with someone with experience with these matters????

3. Continue to drive it as a second driver, add it to your insurance, get a bill of Dale notarized, transfer registration and just go forward until you drive it into the ground and THEN leave it at the train station

Good luck!!

Xoxo
VC

Why would you take a car for services? Take cash then buy a car. Sounds like a train wreck.

You have a defective title:

"Defective Title
Lost/Defective Title Bonds for the Department of Motor Vehicles is a very common surety bond. The premium rate is usually 1% of the bond amount, with a minimum $100.00 premium. This is a relatively simple bond to purchase; all we need is a completed application as this usually does not require a credit check. The common reasons for having to get this surety bond are:

1. Paid for vehicle but didn’t receive title and the lender is out of business

2. The original documentation was ruined in a natural disaster

3. The vehicle is older or custom made so there isn’t a title

Prior to applying it’s important to have this information readily available:

1. Year, Make, Model and complete VIN number for the vehicle

2. Name on the bond needs to exactly match the name of the person applying

The bond amount will be given to you by the DMV, be sure to have it when you are filling out the application because certain states are very particular regarding the bond amount. We normally issue the bond after 1 business day from receiving the application!"

You'll have to contact IL Secretary of State for the Bond amount, its based on a percentage of vehicle's value.  Go to kellybluebook.com or nadaguides.com to get vehicle value.
Allow at least 1 month, (may take longer) for Surety1 to complete search on your vehicle.  It may take 6 months for you to get a title.  And since you do not have title to it,  DO NOT put money into it to fix or improve it.  I would also suggest you park it in a secure location.  
If Surety1 is not to your liking, Google search surety bond companies.
Best Of Luck

Inquire with 17 digit VIN to the DMV of the state in which the lienholder was located, as to the current ownership, and the title status (registered condition - Current, salvage, complete loss, etc). This is considered public information, and some states (not Illinois) have VIN look-ups to aid the process on their Secretary of State's website.

In some (limited) instances you can apply for a "lost title" if you are in physical possession of the vehicle. This mechanism exists primarily to allow a SoS to settle ownership disputes such as the one you describe, and ownership decrees made by a given SoS can be enforced by the SoS's Police, if requested by an aggrieved party (I.e. You).

CW

. . . to execute not only the title but a bill of sale containing language that the vehicle is free of liens.  I have a form that should suffice and would be happy to send it to you if you would like.