I feel you have some misunderstanding of a lawyer's function in real estate transactions. In general, a lawyer will do two major tasks in a real estate transaction: prepare the purchase agreement and conduct title search. To protect your interest, your lawyer has included conditions in the purchase agreement, such as the seller has to show the repair receipt and to clean up the yard. However, your lawyer has no rights to enforce the agreement. Only a court has the right to enforce a contact. When the seller breached the agreement, you had two choices: either refuse to close the transaction or petition to a local court to enforce the agreement. When you signed the closing documents, your lawyer has finished his job.
In your situation, you can inform the seller that if he does not clean up the yard within a certain period of time, you will do it and send the bill to him. If the seller fails to clean the year and refuses to pay the bill, you can petition to a small claim court to enforce the agreement.
As to the $1000 story, you need to make it clear who keeps the money. To me, it does not make sense that the seller's lawyer keeps the money. He is not entitled to the money and has no right on the money. As Old-Cat said before, you may file a claim against the seller,alleging misrepresentation, i.e. the seller told you he had repaired the roof but actually he did not. You may need to hire a lawyer to deal with the lawsuit.
Good luck!