My 2 cents... No, it's not a "do-able idea" as you worded it.
Expedited Freight is emergency freight, it's not regular freight, it's gravy freight that's sporadic and unpredictable. Don't do it until you're ready to commit full time to it.
My 2 more cents... you've been there 22 years... stick it out another 3 years... get in 25 years. Get a bit more of a pension perhaps, then you're what? a bit more comfortable, and you've got that extra peace of mind.
Over the next 3 years you can study what you want in rigs, freight, and the area's you want to run... and gain all kinds of info.
Plus, if you wait, in March you can go to the big Ky Truck Show and get all kinds of info.
Then in the summer you go to the Expo in MI that is organized by EO (ExpeditersOnline.com) and gain even more info about the industry.
You got 22 years now, why not stick it out a bit more,
you've held on for this long.
You say you got 5 weeks of vacation time you can use... the Ky truck show is 3 days... and worth a weeks vacation time if you ask me.
The Expo is a weekend, and while I've never been to it, I've been told by many that it too is well worth the visit.
There's a few more truck shows here and there that you can attend.
But I know what you're thinkin'... You still have plenty of vacation time to use even after attending some truck shows. Take time off here and there to look at different trucks, different programs, and applications that can help you as an O/O.
Don't jump. Study and Research. You'll be glad you did.
The trucks, computer technology, and equipment that's able to be put onto trucks now is mind boggling. Research.
That's just my 2 cents worth.
BigBusBob.