I am sure you have considered this but have to post this.
I have pebble dashing and was put off painting it by my parents who had theirs done a while ago and now have to repaint fairly regularly as the paint doesn't last.
Use 'breathable' paint otherwise any moisture that gets trapped cannot escape and that causes it to flake. Use good quality paint if you decide to go ahead
It's an awful job to do by hand
Got a wagner airless sprayer what I done in 1 full day by hand was done in 45 min by sprayer
If anyone is going to attempt it either hire ,buy,or borrow a sprayer