Oregon to Florida

Then, if it were me I would head straight down I5 to Sacramento,I80 east. The pass on I80 over the rockies is not too bad. Once you get to the heartland you can based on weather decide when to turn south. Of course you miss a lot, but you did say dead head indicating to me you want the fastest way back to FL!

We'll be in Canyonville when we start our return.

We hope to have traveling back with everything attached and in good shape

We used I-10 to southern Arizona, then I-17 at Phoenix north to I-40. Get off I-40 at US 395 and take that north, stopping at Yosemite. 120 west out of Yosemite to I-5. Then north on I-5. You probably want to go west again from the Sacramento area to connect with the 101. I refuse to drive an RV thru the Bay area myself so we aim for north of that area to connect with 101.

By doing this you do miss the Big Sur area but the coast of Oregon and northern California are just as scenic. Once you get to Oregon you will have to turn of the 101 to get to where you are going.

"Deadheading" generally refers to Semis returning without a trailer. Does that mean that you're returning in the "A" without the Jeep, or returning in the Jeep after dropping the "A" off, or something else?

Where in southern Oregon? On the coast or inland??
If around Medford, then I5 south to Sacramento, I80 east as far as you want and then head south. If your on the coast, then 101 to CA 20 east to I5 and follow my previous suggestion. If your in eastern Oregon and again depends how far east or south, 395 or I84 to Salt Lake City area where you pich up I80