As mentioned you can get the permits on line, and you save the fee charged by the permit company. Going from Canada to to Florida the permits ranged from $15 - $60 but the permit companies add $30 to each permit regardless of cost. The permits take from 30 mins to 5 days to get on line depending on which state or province. Typically its 30 mins on line but you should check with each state or province you will be going through ahead of time to see how long it takes and how long they are good for. You will be given a route to follow that will avoid known obstacles like construction, narrow lanes etc. As Jim mentioned, if you are going to be towing a lot in your home state get a yearly permit, saves money and applying every time. In fact check each state for pricing on yearly permits as typically if you go somewhere you will be returning and the yearly permit may not be much more then one way and saves you applying again. You may need to increase your rating on your drivers license because of the weight you are towing.. You can probably talk your way out of the first ticket saying its an RV etc but not sure if you have an accident if the insurance will buy that one. Check the laws where you live. You will be stopping at all weigh scales. My first time I was told I needed a DOT# to obtain permits by a permit company.. I found out later this is not necessary for a personal truck towing your own boat not for profit. With the DOT number I was checked closer and more often at the scales. With no DOT in most cases I got a green light and drove through with out stopping.
All aspects of towing a wide load are simple but just take time. You need to plan your trips ask lots of questions along the way. I have found most people where very helpful with getting my permits. The transports are going to pass you within inches and they do not care if you are experienced or not as time is money for them and a lot of them are not good drivers.I have learned to enjoy the journey on land as I do on the water. Slow down, stay in the right lane and pay attention. As with any trailer every time you stop walk around your trailer , check the tie downs feel the wheel hubs and make sure it all looks good. This is not a race.
Like Bruce said, there are quite a few other posts here with lots more information. As with boating everyone is different how they approach things and how much work they are willing to do themselves. I enjoy towing and getting the permits. Other would rather pay the money and have others get the permits for them .. Still other would rather drive or fly from point A to point B and have their boat their waiting for them. If you are going to tow once or twice for that trip of a life time... get it done by a professional as it it less expensive then purchasing a trailer. But if you are going to move around a lot or follow the warm weather every year then get the trailer and tow your own boat.You already have the truck so that saves the huge expense.. The side benefits are you can easily pull out the boat to clean or repair. You can store it on the trailer.. which for me means I get to stay in the water later in the season and get into the water earlier the spring then the boats lifted out by the marina ( our water freezes here so all the boats get lifted out of the water ).
As with most things on the forum we are pretty lucky being able to be pondering these things
Good luck with your decisions and look forward to seeing you on the water 🙂