Still painting

Most of the inside of our house is painted, now we are working on the outside. We would like to get it done before the winter rains start again. I hear that we have until sometime in October before that happens again. The color will remain the same except for the front door and the shutters, they will be red. The siding on our house is T111, the old style. It's like a sheet of plywood with vertical grooves in it. Being the DIY people we are, we decided to paint it ourselves. We discovered that there is no roller that can penetrate into the grooves of old style T111. (The newer style has shallow grooves and wider surface areas, so a roller works just fine.) So we had 3 choices: let someone else paint it, spray it, or brush the grooves first and come back and roll it. Letting someone else do it it's not in the budget. Spraying still involves brushing as the paint may run in the grooves and you need windless days, otherwise you'll end up painting many things around your house-like cars. So brush the grooves and roll the paint it is. We are still working on it. I'll have to post a before and after pict when done.
We also have to refinish the deck before winter. We had a deck in California so we know what to expect doing that job.

 Old T111 drinking up my paint!