I'm doing ours presently. I'll be on it until Autumn 2017, I expect (no exaggeration). Almost finished the front, which is the most fiddly, but the rest has more area, and access is difficult.
A hairy paint roller will help if the surface is flat. Start at the top and work downwards so drips don't ruin what's underneath. Roll slowly! I nowadays cut in with a fitch around windows, and
one of these for the tricky bits (actually most of the place!). Having a short extension is probably more useful than a long one.
Rafezetter (of this parish) taught me an excellent trick, using oxy-powder intended for washing machines, as a brush cleaner - it's wonderful. AND... if the paintwork is in poor condition, do use something like
this stabilizer first, as it makes a huge difference to the finish quality.
I jetwash first, but it doesn't get the loose stuff off well enough, so the only solution is wire brush and something like a tack lifter to crack off anything that's peeling.
I'm forced to use Dulux weathershield as it's readily available here and can be mixed to colour (it is water-based, incidentally - I think they all are now). Sandtex is better but more expensive. Best of all is Snowcem (Steve Maskery has used it recently). It comes in powder form and you mix it with water. It's very, very tough.
My striker bush doesn't drip much, but the roller does. Much depends on the surface beneath, but a good condition jetwash should remove dried drips from concrete etc. These days I don't bother with a dust sheet outside as it's too much bother.
My uncle, who's been a property guy all his life (now 80+) says this time of year is very good for painting as you get optimal drying conditions as long as the weather is good enough. I think he's right. He also swears by Sandtex, and I came to the same view independently. Dulux is heavily advertised, but thinner - I need three coats where two of Sandtex would easily do. good for Dulux, but not my wallet.
Gotta go - up on the scaffold myself in 1/2 hour or so... :-(
E.