If you want to go cheap, in NC you can go learn how to drive a school bus and get your class B license. You don't ever have to drive the bus except when you take the test. The first license you have to pay for but the bus driving class is free. If you can drive a bus you can drive anything
In North Carolina you can get a Class A non commercial driver license without taking a road test. All you have to do is score higher on the written test. I use to drive tractor trailers with a Class A license, just good for in state driving
In PA you need a CDL for anything over 26001 pounds, just went thru this with a friend that bought a 36000 pound diesel pusher. I went with him to NY to pick it up, spent a couple of weekends training him on pretrip, driving skills etc and then he took his test. PA requires written (computer), skills test and then a road test
I don't think you'll have to pay sales tax twice. Every time I ever bought a vehicle out of state I didn't have to pay tax on it until I registered it in Georgia. If the dealer is taking sales tax then beware of be scammed (why wouldn't that surprise me since you are dealing in Florida).
I bought a cargo trailer in Wisconsin and paid sales on it there. When I plated it in Michigan all I had to pay was the difference between the two states which was 1.5%. Dang, Michigan was higher.