masking

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Using a paint shield is a great idea, and I often use one to keep overspray off of the roof and sometimes trim. You really can't take a lot of shortcuts from masking and need to be sure windows are covered and sealed or cleanup will be extensive. Paint spray travels more than you think. Be sure to mask properly and keep vehicles out of the painting area.

I use a masking machine. It takes rolls of paper and dispenses masking tape along the edge. Makes precision masking go much faster. I always mask the inside of windows with the masker, then use spray adhesive on the paper and apply painters plastic over the paper. This covers the entire window or door and is the fastest way to get the job done. I strongly recommend a masking machine, and a good supply of paper rolls, tape, a can of Super 77 adhesive and a roll of painters plastic.

For masking decks, and concrete, I use a roll of rosin paper. Its inexpensive, rigid durable and has a straight edge. I just unroll along a straight line and can move the sheet as the work area moves. It can even be bent around stairs. Easier and more precise than drop cloths, and masking tape does not stick to these surfaces well.

On most wood siding, you use the sprayer to apply paint, but the job will be much better if you back-brush to work the paint into pores and voids. I disagree with carls recommendation to put the gun in a bucket of water at the end of the day. An airless pump and gun are an expensive investment. Clean equipment daily including the gun filter, and don't forget to put in the isolating oil.