Do I really save much?

I have a stock 360 needing a rebuild. Do I save much money by the time I upgrade to higher compression pistons and I assume better rods or buy a stroker kit keeping in mind that all work will be professionally done and not by myself. Being old and cheap (FRUGAL) is it better to get my cast heads opened to 2.02 and mild port or drop the big bucks for edelbrocks?
I was going to do my 440 but the cost factor doesn't make sense compared with staying smallblock. Would a freshen up on my 727 work or will I need to upgrade keeping in mind costs?
Enough for now, this is gonna be a busy spring lol
Thanks