I want to move to a warm climate. Is it better to leave my current (pretty good) job and just go, or should I keep applying remotely?

TL,DR: As far as finding a quality job goes, is it better to quit a good job and move, or move first and find the job after? I've been applying to jobs cross-country, but I've been getting next to zero responses. Is my current location hurting my chances?

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A little about me: I'm a born and raised Minnesotan that's never left the state. I currently have an IT help desk job in public education, and overall it's a pretty solid gig. Pay is good (but would be more in the private sector), benefits are second to none, and there are definitely some perks. There isn't much vertical movement to be had (both in pay and in positions, it's a very flat department), but I'm overall pretty happy for now.

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...Which is why I'm torn.

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This winter Minnesota was blasted with below 0 degree weather for what felt like an eternity. No, it's not like we normally get balmy weather that time of year, but this winter was especially terrible. We were constantly slammed with snow, and one day we hit -55 (with windchill). MN schools rarely cancel for weather, and this year we had about 5 days of cancellations or late starts. Personally, I clearly enter a moody, tired, and depressed state for about 4-5 months of the year; I've had enough. By the time I finally snap out of my winter slump, it's practically State Fair time, which marks the end of summer in late August. It's mentally exhausting.

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As for where I'd like to move:

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I haven't traveled much, but I've been to Arizona twice in the last 6 years (several family members want to go there too). Out of the places I visited, Gilbert seemed like the right fit. There appears to be a good mix of jobs and plenty of things to do. Housing seems reasonable, with a fair amount of new homes under 250K, something that is impossible to find in the Twin Cities area in MN. Plus, mild winters and lots of sunlight. Sure, summers are pretty damn hot, but so is MN when it hits 95+ with 80%+ humidity. Ugh, the mosquitoes, horseflies, gnats, ticks, and seasonal allergies.

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My experience:

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I have about 5 years of retail sales, and going on 4 years at this school IT job. I also have an associates in IT Management. I am a level1 tech, but I am motivated to learn as much as I can.

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Strengths:

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Proficient in JAMF MDM, Meraki Dashboard, Axis camera installs, Milestone XProtect cam software, Carousel digital signage, iPad, MacBook, and Windows desktops/laptops. Solid problem solver, good customer service skills, and I learn fast. Professional appearance, which helps in interviews. If I get an interview, I feel like I have a good shot at whatever it is. I think my communication and writing ability is pretty spot-on; hopefully you agree.

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Notable weaknesses:

SCCM, Active Directory, and Windows Server. We are primarily an Apple school district, so I barely touch SCCM (less than a handful of times in 4 years, often with help). For Active Directory I basically just reset passwords and add/remove users from groups for access to different things. Lastly, I barely touch Windows Servers due to my role. I do occasionally remote in to servers, but it's mostly for reboots or security camera setups and such; not really any admin-like things. I'd like to learn enough about these systems to be considered proficient for my next employer, but sadly my current role is a bit limited in time and scope.

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What I'm looking for, and my questions:

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• Looking for an internal (i.e. not call center) IT support job in the east valley in AZ. I'd like to make 50K with solid benefits. Is this possible, given my experience (and weaknesses)?
• I did a conference video call with a recruiter, and they basically ripped my lack of SCCM and Active directory experience, to the point where the full-time specialist on the call basically went silent. I was pretty upset by this. Are they right for a 50k job?
• Where / how can I learn more about SCCM, Windows Server, and Active Directory, enough to be considered proficient for my next job?
• Is it better if I move first and look for jobs second, or should I keep my current job and continue applying remotely? If I landed a job, I can probably be there in 3-4 weeks, minimum. Money for the move is not a factor. I just don't want to get stuck in a new town for months without being able to find a job.
• For those that have done this, do you have any logistics advice, such as the move itself, things to button-up in my home state, where to stay, shopping for a house or renting for a period, etc.?

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