Yes. absolutely take a contractor with you!
Do you have a contractor willing to go to the property you don't own (if you are wholesaling, you will not ever own it I assume) and provide you with an estimate/budget, for work he will never perform? If so, take him with you. My assumption is, unless you have him already, contractors are not usually willing to jump from their jobs to go quote projects they won't be getting. I would offer to pay him, but you still may find issues with someone agreeing to it.
Don't be discouraged if your offer gets rejected. Chances are if it is accepted right away then it was too high.
@Brian Pulaski yes I do! He's a local REI contractor, already spoke to him and got the go ahead. He also has connections with many other cash buyers!
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