Red oak has issues with rot resistance if it is wet. In my climate it would work just fine. In your climate it probably would be less durable.
Not sure about white pine. It isn't available locally sip I've never worked with or read up on it. The US Forest Service, Forest Products Lab, has a publication, "Wood as an Engineering Material", that gives all the properties of most woods, including weathering and rot resistance. It is available as a free PDF download, and well worth the time it takes to find and down load.
Re making shingles or shakes: The traditional method is splitting with a froe. You cut the log into the length you want the shingles. Determine the length by deciding how much exposure you want, and multiplying by the number of overlays you want plus one. For example if you want a six inch exposure, with three overlays, 6X(3+1)=24.
You then split the logs into quarters, before you split off the shingles with the froe. There are instructions online, and probably videos on YouTube. The froe will cost about $40. The split shingles warp less when installed because the splitting follows the grain of the wood, eliminating most of the stresses. Once you get the hang of it you can crank them out really fast.