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Roofing & Trim Board Questions

Hello, I have a 25 year old center hall farmhouse type home with a fairly steep pitch. We don't have any leaks in the roof but over the past couple of years 2 or 3 shingles have broken off during high winds. I have asked a few of my neighbors in my area about work they have had done on their roofs and was surprised to hear that even though they only had 1 roof layer on their homes they had the first roof stripped off and completely replaced rather that just putting a second layer of shingles over the first roof. I would think that the cost of stripping and re-shingling would be significantly higher that just putting a second roof on. The reasons given were " there were a few pieces of plywood that had to be replaced". I don't want to be scammed by a roofer telling me that the whole roof has to come off because a few pieces of plywood have to be replaced. Does this reason sound legitimate? Also, the trim boards on my home are in worse shape that the actual roof. I think the builder used MDF some other wood alternative rather than actual wood for the trim boards. They have become somewhat spongy and aren't worth painting any longer. So I was wondering if 1. It makes sense to just replace the trim boards and do the roof later? 2. I would like to replace the trim boards with something that is maintenance free like PVC or aluminum clad wood like was used on the fascia boards behind the gutters when I had them replaced 7 years ago with gutter guards? 3. I am leaning towards PVC but would like to keep the same color scheme. But I understand PVC can't be painted and even if it could there would be a requirements to repaint every few years. 4. Can PVC be painted and if so how long would the paint last on average in the northeast (Philadelphia area)?

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