I did mine in 2000 and like yours, it's due for another go around.
My house is single story 2 bedroom 2 bath so not too bad, but the north end is 2 stories up because it's an addition that was added to the main structure that sits up on a dune ridge. The good news is it's mostly windows on that addition, so not a lot to paint.
When I did it back in 2000, I hand prepped everything using a scrapper and power washer. Then I hand primered it - brush & roller.
Then I used a power sprayer and hit it with 2 coats of Elastomeric. Ended up using 23 gallons.
I intend to do all the work again this time around but will try to do only one side at a time.
Ultimately, when I sell this place, it will be bought by someone for it's location and they will take the house down, so I'm not sweating that everything comes out perfect.
It was white when I bought it and I re-painted it taupe (a shade of tan called Beechwood). This photo was taken shortly after it was re-painted.....