What engine setup (blown small or aluminum big)

Looking it all over it's hard to look past the afforability of the BB. I can get 500 hp out of a BB with just a set of heads and compression, but to pull those kind of numbers with a SB I have to pretty much redo the whole engine. I'd love to go boosted, but I'd have to go with a kit. I don't have the tools or really the experience to piece together a system that I would be happy with. I would wonder how reliable or streetable a 500 hp SB would be as well. What all would I need to look at for a BB swap though to add to the costs? Is it mostly just a drop it in kind of deal with conversion mounts and pay a fortune for headers? Or do I need to worry about specific oil pans, moving other parts around, etc? I know I would need a new bellhousing at the least, and possibly a manual steering swap, but otherwise is there anything that normally gets in the way?