After wasting an entire day rolling just part of one wall, I bought a sprayer and painted the exterior of my house with this Harbor Freight airless sprayer. Following the advice of the guy who sprayed our office building, I bought a smaller Graco spray tip for much better control with very little reduction in speed (this sprayer is compatible with Graco accessories).
https://www.harborfreight.com/painting/paint-sprayers/airless-paint-sprayer-kit-60600.html
Worked great, and I would do it again in a heartbeat. With coupons, I paid about $170.
In my case, rolling or brushing paint on our heavily patterned siding was going absolutely nowhere fast. No matter how deep and fuzzy the roller was, it took six times the work to get into all the crevices. And of course, the walls were clean but the rollers picked up every stray dust mote, feather, bug, and speck of dirt within two miles.
With scaffolding and this sprayer, we got the whole house done in a day and it still looks great. Other than I hate the color, but that's 100% my fault, not the sprayer.
We started out back-rolling, but found that it didn't make the slightest bit of difference. Looked a little worse, actually. I know it's blasphemy, but we just skipped back-rolling for most of the house and six years later I've seen absolutely no issues or differences other than more debris and less even finishes in the rolled areas.
A few weeks later I painted our garage door with this, and it worked great and is holding up beautifully (just had to put up plastic on the inside to catch "spray-through" around the edges and such).
Cleanup isn't too bad, but it's also not something you want to fart around with unless you're painting a large area. And I wouldn't use it indoors unless it's new construction before the flooring goes in. That said, overspray was not a problem at all -- we didn't find any stray paint drifting with the wind or anything, and had very good control with the smaller spray tip.