A lot of people are being unhelpful is this thread.
1) Do you want to spray or do you want to roll? My recommendation is brush/roll because you will have better results, and it will last longer. Spraying is only acceptable if you can immediately follow it back up with a roller for an even coat. (spraying takes 2 people)
2) S.P.C.P.P. (Scrape, Prime, Caulk, Paint, Paint (2nd coat). A lot of paints out there require a second coat for the 10-year warranty (and the first may not cover).
a) Scrape all lose paint
b) Prime all bare wood/siding, places with superficial mildew, rust, etc.
c) Caulk you face off. I've gone through 2-1/2 cases of caulk so far (12 bottles in one case). My house is all older siding though. Caulk all gaps, windows, etc.
d) Paint first coat.
e) Paint second coat.
3) Utensils
a) Ladders (I own 4. 24ft extension, a Little Giant, 6ft step, and 12ft Extension). Get what you need. Buying might be cheaper than renting.
b) Rollers, Roller Covers, Paint Brush(s), Scraping Utensils, Paint Can Holder (for ladder), rags, can opener, stirrers, drop cloth (over cement), etc.
Just start rocking out and you will get the hang of it. It takes a long while. I did half of my house in the fall. I recommend hiring someone to replace major wood rot (I shouldn't have tried to do it myself). Call me if you have additional questions.
