Had a question about my 20 year old Cedar Fence

I'm currently giving my deck some time to dry out, but in the mean time I have an old fence that needs to be redone. The side facing outwards towards the alley was painted red years ago. The paint left on the boards in most places will easily come off with a power washer, but there are some parts of the fence that were more protected from the sun that wouldn't come off easy with a power washer (As I was power washing my drive way and gave it a try).

My question is what to do about this problem. Should I just do a mixture of scraping and power-washing?

The inside of the fence was never painted and is just the normal grey color. Would also appreciate any information on what to do with this.

My buddy has an airless sprayer to use when I have the fence prepared. Also, should I wait to do this when the weather is dry? I would like to do it soon, but it has surprisingly been raining in Dallas this week. Should I wait for the rain to stop?

Any ideas on stains/paints to use would of course be helpful as well. Would prefer a dark stain/paint. I'm not sure this fence will make it more that five years, so this may be the last go at it.

Thanks for any help

Mike