Your numbers would cover any truck and trailer of your own but I can't say for sure how the other trailer would work.
A Class A CDL License is required when the combination of the Gross Vehicle Weight Rating (GVWR) totals 26,001 or more provided the GVWR of the vehicle(s) being towed is in excess of 10,000 pounds.
Here is where you can do it online. The unfortunate part is that you have to go through a safety audit because you will have to be interstate (crossing state lines), where I am intrastate for now because my work is all local.
Hope that helps a little