Playing it safe sounds like the right thing to do. reducing risk, limiting your exposure, reducing the downside – all good things to do. Or is it? In some cases, limiting the downside may be the risky thing to do.
Take the case where you place so many caveats on an offer that your customer takes all the risk in the deal. Sure, it's the smart thing for you, but it sucks for your customer. Or what about the service warrantee where the fine print and limits on service and support are so great it's less likely you'll have to repair than it is you'll have to serve.
Who benefits and who looses? If you think in those terms then you do, your customers will go elsewhere.
Do you want to be loose with your Agreements and offers, recklessly risking everything on every deal? No. You just don't want to be so risk adverse that your contract, warrantee, and service agreement read like post-filed legal briefs, limiting your exposure and tying the hands of your customer.
Have you seen or accepted a one-sided agreement – an agreement where you carried all the risk? If so, how did it make you feel?