@Alex Nelson finally something I am an expert on! I am a field rep for a paint company and work with professional painting contractors for my 9-5. I also sell Graco and Titan spray equipment as a component of my job and have painted professionally in the past.
I would highly recommend an investment into an entry level commercial paint sprayer for anyone doing renovations on a regular/semi regular basis. The amount of time/energy saved by masking and spraying (when approached correctly) is immense and you will justify this cost in a single interior/exterior repaint. For example, the image below is my current rehab at my own home. Using a 3M M3000 Hand Masker and my Titan 440 Impact, I masked and sprayed a full prime coat, and two coats of finish on this project with about 2 hours of actual labor. This would be for multiple rooms of window, baseboard, and doors. To accomplish this same project by hand (roller/brush) would be 5x the time and the finish would not be as appealing.
A decent light duty commercial airless sprayer will run you between $800-$1000. I would recommend staying away from the big box or DIY sprayers (plastic body housings) as they are not meant to be used professionally and often cannot be repaired. Take a look at the Titan 440 Impact or the Graco 390/395 to start.
For the folks in the thread above saying that they made a mess of things when using a sprayer, its all about the prep! Use drops, masking paper, and adjust the pressure settings on your pump. Use the recommended tip for the paint you are spraying and don’t try and be a hero on a “one heavy coat” application.
I also recommend the Graco Ultimate 2 Handheld for those small projects. Sprays with the efficiency of a true airless pump and is infinitely repairable. Cordless and Battery powered for those projects where only a small amount of paint is needed and power supply is an issue.