I Got my CDL just to move my family across 4 states - I have questions

I live in Illinois, and Illinois is flat out too expensive to live in anymore.

Moving is expensive, too. Allied want 12k to move me. PODS are not an economical option, as I'd need 6 of them..

ABF U-Pack only has 28-foot trailers, and I'd need 2 of them @ $3200 ea = $6400

My total bill with the following Semi-Rental-Move-Myself-Plan is $3977.50 all-in. (CDL Application, Truck and trailer rental, mileage, DOT physical, Practice costs, road test costs, 363 gallons of diesel)

BUT, I HAVE to leave Illinois, or I fear I'll never get out. Got a wife and two kids, and the kids are in 5th and 6th grade, so its now or in 5 years, and by then I'll be older and more cranky about life..

I work for myself in computer consulting, and have good business financials that allowed me to establish a credit account with Ryder (Commercial), and I have the Penske Owner/Operator packet, but Penske requires you to have your own Semi insurance policy.
Semi insurance from Progressive, paid on an annual policy, would cost around $650/mo, and is cancel-able anytime., but ties up some cash. So Penske is a worse-case option.

Rental prices for both Penske and Ryder are around $1000/wk for the tractor + .15/mile, and $500/wk + .05/mile. I figure I'd only need a week rental...

I'll rent a D/A Sleeper, and a 53-foot trailer. (or 48 when I get closer to final load calculations)

I've rented a 26-foot straight truck from Penske in 2003 from Chicago to Virginia, and a couple of U-Hauls before that.

I have my Class A Air CLP, and am taking my road test in a manual transmission next Monday, and I expect to pass.

I have completed 5 hours of driving, parking, and other skills through various means at a total cost of $300 so far. I have driven a 53-foot trailer hooked up to a D/A 10-speed around a gravel pit for 2 hours, and spent 3 hours driving, backing, and parking in an old 6-speed syncro Coke daytruck with a 28-foot dry box.

My load is household goods and a properly blocked and braced 99 Lincoln Town car (maybe), and will probably not exceed 5 tons.

I've slid the tandems, hooked and unhooked trailers, researched scaling, and the Bridge law.

I got my Medical Cert signed off on today.

I've watched over 12 hours (ad-nauseum)
Youtube video of Semi wrecks,
good drivers,
bad drivers,
the full 30-minute Texas Road test,
what to do if you have a steer/drive/tandem blowout,
how to make right-hand turns, left-hand turns,
what lane to be in when turning,
semi-driver gets mugged at rest stop
videos about setting up for turns, b
locking the right lane,
jug handles, buttonhooks,
completing and keeping logs, 24 hour resets, 34-hour resets, 11 hours, 14 hours,
US 60 hour 7 day week cycles, 30 minute rest breaks,
fuel and road tax info (IFTA)

I've read and researched articles from thetruckersreport and other to get more of a feel for driving.

I've ordered my DOT approved "Not For Hire" magnetic stickers.

I have a dash cam, scanner, CB, smartphone, Baofeng BF-F8HP, and tablet.

I've downloaded the Keep Truckin app for logging, and Sygic truck (paid), and use them when driving in the car.

My wife says I'm crazy, I think it would be an adventure. I want to take my 11-year old on the trip with me.
My biggest fear is dealing with turns in that 53-foot, and clearance issues.

My route will be 1020 miles from Rockford, Illinois to Eastern Colorado Springs, and 1020 back to return the truck and trailer - departing first week of June, 2018.

I'll take the "house" to Colorado with my 11-year old.

While I'm driving, my wife and daughter will stay with friends in IL.

When I return to IL, I'll return the truck and trailer, then all of us will drive to Colorado in the family vehicle.

Am I missing anything?

Any newbie advice y'all can give, or am I in way over my head.

Much Appreciated,

-Just a guy who does not want to be taxed to death in Illinois.

 

Chinatown - That was something I had not even considered...! thank you for the suggestion..

So I did some quick planning..

$300 for the plane
$200 for a hotel night
$1169.10 for Penske for each leg
= $2838.10 total

HOWEVER

My wife requires that I drive her and the kids in the family vehicle on the final trip from IL to Colorado as she and the kids would stay in IL at a friend's house until my return, so that's another $300 plane ticket for me to get back to IL from the second run:
= $3138 total vs. $3977 the CDL route = $839 savings

But, it's a 1.5 hour cab ride or shuttle from Colorado Springs to Denver airport x2, plus 1.5 hrs cab ride or shuttle from Chicago Airport to Rockford x2. Plus the waiting in airports, and being alone. I think that would take up all the savings.

Also, I think it would be a great experience for my 11-year old. That's a great age to begin making some lasting memories..

Sound fair?

 

Yeah, your right, not 15, but I'd need 4 to 6 for sure.. but cubes/PODS are at a premium price and blow the Penske 28 foot quote right out the window...

 

Don't get me wrong - IL has a lot going for it. unfortunately, it's just not in alignment with my needs anymore.

I grew up in Montana shooting guns and riding dirt bikes.

Grew up a bit more, moved from Montana to Chicago to see the big city life. Found a cute gal, married her took her to Virginia away from her parents and family so we could start OUR life and discover and build our relationship.

Impregnated her, had some kids, moved back to IL to be closer to her aging parents.

Her parents ended up moving to Vegas because of Illinois taxes, her brother is moving to Vegas also.

I'm wondering why I'm still here when nobody else is, and I just want to shoot guns and ride dirt bikes again...

Oh, and actually retire in a home I (mostly) own that is paid for and I can pay the taxes with SS or retirement... and STILL shoot guns and ride dirt bikes!