no you dont have to do smooth first...its just easier....I use booleans all the time and yes your way dave is a neater geo but a lot of work. I have used both methods and it depends on the geo. If you look at the jetpack on my marine it would have been a lot of work with the split poly tool...so I smoothed first and did it the easy way. You also have to presplit the 2nd surface because you cant do it after the boolean...as I said it depends on how complex the geo is in which way I do it.
bullet1968
"A Darkness at Sethanon", a book I aspire to model some of the charcters and scenes