This seems risky; you should have an attorney review the agreement and the overall situation to determine if this is the best option for you. If you're sending the agreement, it may be worth it for it to be returned to you signed. In situations similar to this, I always ask myself if it's worth the risk that it will be challenged later. An attorney could review your agreement and answer your questions over the phone, to keep costs down. Good luck.
Answer given for general advice and is not a legal opinion, which would require an analysis of the facts and circumstances as well as the applicable law and regulations.
In many cases, given the factual scenario, this could be held to be an enforceable contract. However, if the agreement breaks down and there is a dispute, wouldn't you prefer to not have to endeavor to prove the existence of a contract? Rather than using an e-mail reply for the acceptance of the agreement, why don't you convert your contract to a PDF and use a program like Adobe EchoSign. It is free to use (on a limited basis) and gives the parties an opportunity to endorse the agreement with digitally verified signatures.
I understand your wanting to keep the arrangement informal, but your plan creates unnecessary risk for both of you. If this person is wary about signing a contract, he or she may not be someone you want to get involved with anyways. It's probably not worth the risk - I would formalize the contract and have it signed by all parties involved.
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This does seem risky to me. Although doing it the way you are suggesting COULD work, what if it doesn't? As this looks like it is for potentially a large amount of money, I would strongly recommend getting an experienced Contracts attorney to review this for you and to provide you with some advice on how to proceed. The other choice is to sit down with the other party and tell them why you want these changes made. If they make sense, the other party should agree to them. Best of luck.
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First you should have contract/business attorney as suggested by other colleagues to review specially if "important" to you whether digital signature or hard copy. You can't hide any provisions.
Second "yes" in a reply does not state anything nor does it mean anything.
Yes to having Received or read or agreed to your email, or it's attachment, or some self serving contents in your email? Yes to what exactly. Right there you many possible answers! So it's unclear.
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If it is important to you to be able to enforce the terms of the contract should the other party not follow through, then I would highly recommend that you get more than a "Yes" e-mail reply. A properly executed contract would benefit you and the other party while relying on just an e-mail will just create avoidable uncertainty. I would not assume that the other party would feel more at ease without a signed written contract. I believe how threatening a written contract may appear to the other party will depend on how it is presented.