I'm not a huge fan of pressure washing, simply because it doesn't get
ALL the grunge and peeling paint. You'll want to go over everything
after washing and make sure everything is clean and any loose stuff is
removed.

#3 will get you by for a while, longer if your temp range isn't very
wide. I'd probably switch 2 and 3 -- caulking the small cracks is
fine.
And if there's any bare wood, you'll want to spot prime before getting
into finish coat.

As for brands, a lot of them are regional so sometimes it's hard to
recommend. I've used Porter, Sherwin-Williams Superpaint... had good
results. There was a Benjamin-Moore line I used but I can't remember
offhand which. You're better off going to a regular paint store.