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I have a similar style roof. I also have easy access to the attic, making it easy to look at the inside of the gable ends. If you can't get in your attic for what ever reason, you are stuck guessing. If you feel like you are getting in over your head, a carpenter may save you from serious damage to your home.
I would expect to find trim board or siding (typically Cedar here in Seattle) over the rafter which in my case is Douglas Fir from the late 40's or early 50's. I would not count on lap siding to have the strength to hold screws in a storm. You are on the right track to put threads into a structural member such as a stud or rafter. Seal with a quality caulk (I prefer paint-able caulk, not Silicone, which will not hold paint) to prevent water leaking in though the fastener penetrations.
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If the well is dry and you don't see rain on the horizon, you'll need to dig the hole deeper. (If the antenna can't get the job done, an amp won't fix it.)
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