Transporting Multiple Machines

I am the O/O of a firm that provides custom harvesting services for dairy farms. Most work is regional, within 150 miles of home. For this I have a 2007 T800 and a '99 35 ton Dynaweld hyd detach. Normally I will shuttle the chopper to the customer's farm a day in advance, then go home to retrieve my F-250 CCSB and fuel trailer.

I have the opportunity to pick up large job about 800 miles away this year, but the cost and time frame prevents me from making the extra trip. My solution is to leave the fuel trailer behind and keep all my spare parts, tools, and a 300 gal fuel tank in my truck bed.

The problem that arises is the length of the two units I need to transport. With a header, the chopper is approximately 31 feet long and the pick up is about 19 feet. They will not fit on my detach.

I see there are extendable lowboys available, but the lack of a floor on the extended portion would be an issue.

Hiring the trucking out is not feasible as the timeline of agriculture is far too demanding and unpredictable. It is not possible to wait for transportation for several days upon completion, nor can I afford to pay a trucker to wait on me for 1-2 days.

What are my options?
TIA!
Example photo below for illustration. My machine is the same physical size, just one series older.

 

Assuming minimal interruption, 20 days.

Flying a driver back and forth would be cheaper than trading for a new trailer.

 

With respect to ag exemptions, there just a few I am aware of. Some states allow 10% over gross on non federal highways if leaving the field or site where scales are not available.

Also, farmers are exempt from hours of service, drug testing, and CDL requirements when operating intrastate in a 150 mile radius.

None of this applies to me as the truck has commercial plates, I am operating interstate, and my farming enterprise is separate from the trucking and harvesting entities.