"I am going use a Wagner airless sprayer to pint everything."

WHY?

Why not? I just used a Wagner I'd had for years and never used, to paint the inside and out of a 10x10 foot storage shed I build. Then used it to paint the supports and new pegboard ceiling I put on a 50x9 foot patio. It did an exceptional job on both and a hell of a lot easier than using rollers and brushes.

go for it,I don't guess it makes much difference which goes first

Spraying the trim is worthwhile in my opinion because you don't have to cover the walls to do that...you can just get overspray all over the walls. But, then going ahead and masking off all the trim in order to spray the walls isn't really worth the effort, at least not from the perspective of a professional. Spraying always seems like it's faster, but you need to decide if doing all the prep work is really going to save you any time in the end. Plus, don't forget the walls need to be rolled whether you spray or not. It's almost impossible to spray walls perfectly even, especially with a Wagner.

Paintguy, thanks for the help.

I've been playing with the idea of renting a sprayer. Would a quality sprayer negate the need to roll the walls anyway and allow me to better control overspray?.

He is wanting to paint the walls, trim and shutters, which are not removable. There is not that much trim except for the facia board and whatever you call the area under the eaves of the house. It would seem this would really be a lot easier to spray. I'm thinking I could spray a lot of the walls, just don't know how close to another color I can spray without getting overspray on it. He has a lot of shutters I've painted once already and it was a real pain.

Here is the plan I had:
1. spray the shutters, don't mask anything.
2. mask off the shutters and spray the walls.
3. hang drop cloths on walls and spray the facia and eaves.
4. hand paint the window trim.

comment?