Every time I start up my carb'd Roush 342, I smile. When I get home with my son from a cruise and we smell like we did some laps at Sebring... fuel and all, I love it. It is streetable, doesn't overheat and is a blast to drive. I have 17's, but would eventually like an additional 15" set like you are describing. With 315's on the rear, I don't have traction issues and the tires I have currently are pretty old. I quickly ease into the power... no need to mash the throttle on the streets and paint Goodyear lines (remember I have my 10 year old with me).
Would a turnkey efi 5.0 be great... can't say it wouldn't! I've had a few 4.6L Stangs and also a 2014- 5.0. They sound good, start up when you ask her to and perform. For me, as someone said above, there is something about the sound at idle and also under load that a Coyote just doesn't seem to produce compared to the other choice.
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I lack the space, talent and time to be constantly wrenching. I do have a good performance shop that is in my city.
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Once the engine and carb are set up, how much "wrenching" do you really feel you would have to do? With a good shop around, I think that is justifiable.
Talk to owners of both and see what lines up with your wants/needs the most.
Buy what you WANT because there would be nothing worse than you having an issue with one of the setups and then wish you had gone the other way. Good luck... and I don't think you can go wrong.
p.s. Will you have a bigger smile at a gas station when someone is asking you about your car if it's a 1965 build type of thing or modernized?