@IHawks we can PM if it decide to take that route, but I am writing a high level summary here since I think other can benefit as well.
The way our boats ( 190 to 240) are set are fairly easy to tow with an F150 or above. That opens the door to tons of contractors who are semi professionals ( aka hot shot). Enter the world of Uship. This works almost identical to uber. It charged about 25% of the fare to connect you with someone who it willing to transport your item.
Based on my experience is a lot about how lucky you are. What I mean by that is say you want to move a boat from Florida to Chicago. Best case scenario for you is someone from Chicago who just delivered a boat in Florida and need to come back. This person is very likely to give you a killer deal. Say something like $0.75 per mile. Now that being said anything below $0.75 is a red flag in my book. I personally will not even move a Jetski for less than $0.75 per mile, so if you get an offer on that range make sure you are real comfortable with the arrangement.
If you wanted to maximize your chance of being lucky the best way is to be flexible with the pick up and delivery window. That will get the best possible price. It also help a lot if you are in rather remote location if you are willing to pick from a "HUB" For example, if you are 2 hours north of Chicago it might save you like $300 if you drive the 2 hours to be pick up from Chicago.
It is important the boat and trailer are ready for a long trip. in October I traipsed a forum members boat from Oregon to Texas and the only incident was lost screw on the trailer fender. But the trailer was serviced and in top shape. Last thing you want is for a bearing to give up halfway or in middle of mountain with no cell phone reception. Most hot shots are equipped to deal with it, but trust me it is not good for either the driver or you. The longer the trip the more effort you want to put that trailer is a good shape.
the person advice is always to go pick up your own boat. It is true that if you factor in fuel, hotels, your time and wear and tear on the truck it is not worth it, but there is something cool about driving cross country to pick up your new boat. But maybe that is just me who drive to from Texas to PA to pick a tower instead of shipping it, LOL