Did mine back in 2000 and 19 years later still looking good. Mine is only a 1 story mostly block house with some wood siding.
Prep work involved pressure washing first and then a scrapper/scapula to remove anything else I could scrape off. Then I applied a primer by hand (roller/brush).
I used two different types of primer - one for masonry and one for wood.
Then I covered all the windows with a clear plastic self adhesive film that came on a roll to mask stuff off.
Then using a paint sprayer that ran off a gas engine compressor I applied two coats of Elastomeric paint - 24 gallons total.
I sprayed the second coat after waiting 24 hours for the first coat to set up good, but I think you could go in sooner if you wanted.
Once the prep work was done the actually spraying was fairly easy and straight forward.
This is an example of the paint machine I used:
Most professional painting contractors I know nowadays use electric spray machines more like this one:
Even though the north side of my house is an overhang (it sits on a dune ridge) and could be considered 2 story, most of it is 1 story. If I had a conventional 2 story house, I would probably hire someone to do it as I'm not too hip on spending time up on a ladder more than necessary.
The manager at the paint store was a friend of mine who I had done some favors for due to my position as a store manager myself at a fertilizer supply business so I got a very good deal on the paint, which factored into my decision as well. Elastomeric isn't cheap paint, but I can attest to how well it holds up to the elements - and in particular my proximity to the coast.
In fact, I'm prepping my front concrete steps right now for an Elastomeric paint application.
I'm using a product known as a gripper to help prime some areas where the old paint had flaked off some.
Will post pics later....good luck however you wish to proceed!