Supercharged or Stroked 360

So instead of Both, it's None-of-the-Above ? :)
But yeah that's a good thought.
Keep this engine complete as a package for either to sell it as is, or use it in another project one day.

Then again, going the Hemi-route, besides the power steeringbox changeover, also means a crapload of rewiring has to be done, stock computer or aftermarket (steep learning curve), actual fitment of the engine in the tiny engine bay, custom enginemounts, expensive headers, custom oilpan, custom oilfilter setup.

How long will the car sit idle in the garage when all is said and done?

A built-360 will be much easier/quicker to install and have fun with.

Right so originally, a year or so ago, I wanted a Gen III Hemi. However, when I factored everything you mentioned above, including cost, I decided to go small block as it's a drop-in situation. I was even contemplating stroking it. Then I saw this engine for sale and said it was way too good of a deal so I jumped on it quick and bought it. The whole point was to get the Dart fun and done so I can start enjoying it as a grad present to myself. The shop is taking a little bit slower than I'd like but if I did it, it would have taken me 2-5 years to get it anywhere near this point.