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Stripping is a good idea, and it gives you the opportunity to check out your sheathing and either repair and refasten it with ring shank nails or go over it with additional sheathing. You want a roof that will support the fasteners that hold on the roofing material.
I have been known to cover whole roofs with Ice and Water Shield products, if the price seems reasonable. This can be considered good practice in areas where you might see part of your roofing blow off, as you will still have a roof membrane under everything else.
Use a nail that goes completely through the sheathing if you do shingles, and use plenty of clips and or screws if you go metal. Definitely go with an architectural shingle if you go that route, but consider that no one has ever regretted going with a metal roof if it was done right.
The metal roof on my house was put on before 1900. I coated it once. I built my shop less than 20 years ago. I will be redoing the shingles within 10 years.
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