Hello all! First time poster, several times lurker

THIS as been the most informative resource for me thus far - the AK FAQ thread was awesome! so happy to have come across this forum.
I am so sure you regulars are sick and tired of the "I'm moving to AK, can you help me?" post...and here is another one! Sorry and THank you in advance.
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I have looked back and read many a post about moving, but some are years old and I don't know if some info still qualifies (like about employment and such).
Him: seasoned truck driver, now driving in Oil industry.
Me: self employed massage therapist, no real experience in any other field than bartending.
We are: from North Dakota - used to 9 month winters, short days, well well below zero - am I sufficiently prepaired for what an alaska winter is like? At this point I love dark cozy winters and being snowed in, time for crafts and DVDs! I I can totally handle ND winters, I expect AK to be a few notches above what we already experience, accurate?
We enjoy small towns. We are used to planning life around weather and wait for items you want, or a chance to get somewhere to get them.
Fast reliable internet is important to us.
We will be travelling with pets - yikes. Have 1 older medium dog, 2 small dogs and 1 declawed cat. I understand renting will be a challenge, do you think impossible?
We would LOVE to rent a house. Tiny, cramped and 'not that nice' is fine with us - we don't expect miracles with a budget AND pets. We really wouldn't mind being out in the boonies a bit (but I suspect ND boonies are a far cry from AK boonies!!)
So far we have been drawn to the Kanai 'area'. Been researching Homer, Anchor Point, Seward (BEAUTIFUL!) and Valdez, - if I'm moving to alaska I would love to be positioned near ocean and mountain range - have seen enough flat prarie
We have found something he is qualified for in Homer, and a home in our range in ANchor Point, but nothing definative at this point. I also like Sitka!
I would like a lot of things to do, we are interested in snowmobiling, I like arts, outdoors and active town life - like bars (just one good podunk bar is fine with us), events, street faires, town groups/committees and celebrations ect. Can you think of a town with a good combination of the above?
About the move: Here is what we are *thinking* - using kanai area as an example.
**please let us know if you see any rookie mistakes!
Using online to secure job for him, then housing. Maybe his employers would be 'in the know' about local places, otherwise using a variety of online services like craigslist ect. Then finding something for me. I would love to do massage in a resort place, but open to any place that hires me
Liquidating household junk that weighs you down
Depending on relation of home to work, and if we end in a quite small town or place with taxis - parking my vehicle ('03 trailblazer with 100,000 miles) at my parents for at least time being.
Buying decent sized trailor, loading 2 snowmobiles and 1 motorcycle (for the summer!) and what else we can into it, also loading his truck with a topper.
Packing animals, driving to (I believe Prince Rupert we saw was the start of the ferry system - might be wrong.) about 4 days drive.
Taking Ferry to the next point - might be wrong again...seward or homer it went to..details...or whittier...anyway, the last stop closest to wherever we get both a job AND housing.
And there we are. estimated to end of line - 1 truck, trailor and us at about $2000 for the ferry, and $1300 for 4 days driving. Can bring animals on ferry?
We are thinking about a move in a couple months, spring/early summer, mid summer maybe. THe work he found was seasonal - ending in Oct. Then he would find something simple like bartending through the winter, back on truck next summer. Ultimately, in the future, we would love love love a houseboat.
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So there we are. Do you see any newbie red flags? Rookie mistakes? Disasters in the making?
Are we missing something important?
Do you know of another area/town worth at least looking into?
To anyone who made it this far - THANK YOU for taking time to read this incredibly long winded post...bad habit...and I hope you can take a moment to reply with any of your insights or experiences!