Most of the painters I know are teachers that do it in the summers.
On the painting the deck, I personally avoid painting any wood outdoors. When it starts to crack and peel up, it looks horrible and is a PITA to deal with. Last year, I had to repair my fence, and protect some wood outdoor furniture. I was told by a few people, that ready seal was the way to go. Because I had some different colors/ages of wood, I went with a darker stain.
Overall, it turned out really well. I tried multiple methods and ended up using a sprayer with the most success (similar to a wagner power sprayer type thing). The biggest variation I had in color, was when I was brushing it on, and the bottom of the can had a lot more tint than the top - which is on me for not keeping it stirred.
Anyways, it is something to consider. You could test it on the different woods and see how it turns out.
https://www.readyseal.com/