Advantages of a stroker for daily driver

As much as I love a hemi I think I need to stick with a 360 a hemi swap is way to much for me.

Just picking up a motor/transmission won't cut it unless you've got a complete parts car to swap out all the mechanicals necessary for a V8 and a place to do it. Mindful of your statement of the part time job, you are far better off trading off your car for a small block based one, or just going with a hairdryer on the slant as you get time and knowledge.