Whats better,grinding a crank or line boring?

Staying with the 400 main size is more economical. Boring out to the 440 main size costs some bucks but opens up the opportunity to better bearings and better cranks. What you're building sounds pretty mild so if it was me I'd just stay with the smaller bearing size.

I think the best path lays in getting a good crank with 400 mains and a 3.90 stroke. That way theres no fussing around with the block and the crank just drops in.

As far as bearing selection,theres enough for me.

Pretty mild? It's borderline for the street but mild for a race engine I guess.