The advice above is important. Yes, flee south to get ahead of the weather, but most of the Balkans are mountainous and not conducive to winter motorcycle travel. Even otherwise-wondrous coastal regions (e.g., Croatia, Italy) get windy, chilly and wet. I've scooted through those areas a couple of times during November and December, and there were definitely times I wished I'd planned better.
An Iran stamp will attract attention at the US border, but a calm explanation without defensiveness will allay their concerns. Depending on how long you plan to spend in the US (look into this carefully, since the rules about visa waivers are a bit weird), you may find it easier to apply for a visa long in advance, before you have to include Iran in any list of countries you've visited during the last couple of centuries.
Most of your concerns (carnets, getting from Russia to Alaska, InReach vs. Spot locators, etc.) have been addressed repeatedly in these forums, so using the site search should be productive.
Hope that's helpful.
Mark
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