Potential pre-retirement in 2 to 3 years

That's a good plan. OTR jobs are easy to get if you have all the endorsements.
New driver job market is a little tight right now, but that will change by the time you're ready to roll.
Being in the Orlando/Daytona Beach area, your best bet is for refrigerated or flatbed companies, since you want to stay on the road for long periods of time.

 

I've only been local, so I can't help you with question 3, although I suspect if you're going to be taking extended home time they'll want you to return your truck to a terminal and clear your stuff out, so the truck can be rolling even though you're not. As far as questions 1 and 2, my experience says yes to both. I got my CDL at age 57 more or less as a lark, but got hired by one of the major LTL carriers, and it turns out I really enjoy driving, so I'll keep on doing it as long as if fits in with the rest of my life.

 

To answer all of your questions, YES to all 3. As far as your first year out of school don't expect to be treated the greatest that first year..most drivers don't stay at their first job more than 6 months to 2 years with a few exceptions. Get your year or so of experience at your first company and move on to higher paying companies. There are a few exceptions. I stayed at my first for about 5 years, I should have left after 2 or less because I was leaving money on the table with a higher paying company that required more experience As far as your age you are fine, I started trucking at 50 years old .There are quite a few OTR few companies out there that will love you if you plan on staying out months at a time. You can do that and take a week or so off. Sounds like you got a good plan in place, good luck!

 

Yes most companies like old guys.Once you're licensed and get some experience you could even sign up with a temp service and sort of work part-time, or stay out as long as you like.

 

I know you have a couple of years to go, but I'll give the names of some reefer companies that may be hiring when you're ready to roll. All these usually hire new cdl school grads, but have tightened up on hiring during this recession. Probably be back to hiring new cdl school grads by the time you're ready.
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Windy Hill Foliage, Inc.
35814 County Road 437, Eustis, FL 32736
I don't think this one runs West Coast.
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Home - Premier Refrigerated Transport
Facility in Zellwood, Florida
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May Trucking Company – Performance. Reliability. Leadership.
Runs 48 states; coast-to-coast & border-to-border.
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Kold Trans Refrigerated Transportation & Logistics Trucking …
Facilities in Winterhaven & Miami.
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J&R Schugel Trucking – J&R Schugel Trucking
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National Carriers | The Elite Fleet
Hiring all over Florida.
National Carriers is a motor carrier that offers a variety of transportation services across the US. Learn about its history, opportunities for drivers, and customer focus.
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Welcome to WEL Companies - Your Transportation Partner
Facility in Winterhaven, FL
WEL Companies is a family-owned trucking company that offers CDL truck driving jobs, TL/LTL, integrated logistics, and warehousing services. Apply now and enjoy flexibility, respect, technology, and earnings with WEL Companies.

 

Home - Leonard’s Express (leonardsexpress.com)
200 Avenue B NW, Winter Haven, FL 33881
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Freymiller | Logistics and Transportation Experts for Time-Sensitive Freight
Finishing Program -
Recent Graduates
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Prime Inc. | Freight Transport & Logistics Trucking Company
Prime has a couple of Florida terminals & some drop yards.
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Nationwide Express (nationwidexpress.com)
This one is dry van, but it's near you.
MAIN TERMINAL: 5350 N Pine Hills Road, Orlando, FL 32808
WE COVER 48 STATES
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