I Live in MA. I purchased a home here in 1996. The house was built in 1986. The color of the house is cape cod grey or a color similar. In about 2004 the western side of the house started to peel and chip. The white trim is black from mildew. As a side note, we have a inground pool in this area. We also had woods and thicket starting to encroach on our back yard. We have since removed and expanded the yard. Partially for looks and the other part to reduce any moisture that maybe affecting that side of the house. This side of the house is in the sun now most of the time. Our south side of the house is in about the same condition. The house is sided with cedar clapboard. The front of the house is cedar shingles which are holding up very well. We had college pro painters come in around 2005 ( that probably didnt help in the long run) , Now it is 2011 and for the past couple of years the degredation has started all over again. I`m looking for advice on how to repaint the house. I understand that the prep work is the hardest part in order to have the finished product be of the highest quality as well as durability. I have some painting experience...Understand some of the mechanics. Here are my questions.
1. Can I carefully power wash the house and if so, what do I use with the preasure washer?

2. Oil based primer sealer? or latex.
3. Anything you folks can add would be greatly appreciated. I`m in no rush to complete this job. I have the summer and have no problem doing a section at a time so the job will come out well. Thank you.