Lead on a 408. Should I do it?

While its fun to dream of all that power just don't consider the motor. What are and in what shape is the rest of the components of the drive train in? Big torque output (what a stroker does), unrestrained throttle foot and unexpected traction will start popping 40+ year old parts like a pan of Jiffy Pop on a hot burner...
I'm pretty leery of "deals" like this. More often than not they end up costing way more in the end than using what you already own. Without knowing the components of the motor, cam specs, head flow #s, quality of machining ect... ect... it's a crap shoot for any of us to advise you. Do you know and trust this engine shop/machinist to give you the straight poop? Do you know all the ins and outs of properly building a stroker motor and all the questions that need to be asked and the answers verified by someone knowledgeable that you trust with your $? I'd pass.
Don't know what is behind your goal of 400 HP but it shouldn't be too hard, or expensive, to get that 340 to make very respectable and street usable power.

Great advise. Thank you. 400hp was a number I felt was attainable on my 340 so wanted to get close to it.

I don't know much about the ins and outs of a stroker. That's why I am here posting this. I knew without knowing more it would be hard to say if it is a good deal. Really I guess I just needed a little info\education on what to look for and what questions to ask.

Trust in the machine shop is moderate. He has built a few motors for my dad and specializes in heads. I think he will tell me the truth in what will need to be done before putting it on my car. if anything he will encourage me to let him rebuild it.

I guess my biggest thing is I don't want to put all this time and money in my car only to want more power down the road.