length is going to be your enemy. Legality is a whole problem in and of itself. I have followed it in CA for the last 20 years and have seen the vehicle code language change and interpretations of the code vary by enforcing departments. The one common for CA is the 65' limit.
I have explored doing what you are suggesting but I am already at 61' with a 36' MH and chevy Silverado toad. While current CA vehicle code is being interpreted as legal with the two I cannot stay under the 65'.
On a side note I have seen an increase in truck, TT, and utility trailer going down the highway safely and have not seen one on the side of the road having a conversation with the highway patrol.