Legal Question in Real Estate Law in Illinois

Honestly, the very fact that you have posed this question confirms that you should have an attorney involved. Generally, an attorney would not file any of the documents you mention. The only document that would typically be filed is a Memorandum of Agreement, which is sufficient to put parties on notice of the pending transaction, without disclosing all the detail that most people would want private. If you were to file signed deeds, then you are arguably completing the conveyance and, depending on the content of the deeds and the order in which filed, you may inadvertently give up your legal rights. Further, you would have to account for transfer taxes with the filing of the deed(s). So much more that I expect should be covered, but that is best left to an attorney you hire.

Please take this in the spirit intended, but you really need to hire an attorney to assist you with this. Your understanding of what needs to be done is completely incorrect. You may be prejudicing your ability to enforce the contract in the future. The cost to hire an attorney will be far, far less than the cost to repair the damage if you do not.