I've done the trek 3 different times in I guess it would be 2 different ways. The first time was in June of 2017, I bought the boat from a yacht broker as well as went through my credit union and used a surveyor on top of that to act in my place essentially. Everything checked out on the boat, so my credit union wired the yacht broker the remaining money and then the boat was mine. It was about a week before the 4th of July, checked with a bunch of shipping companies, UShip and several others... all of which said they were going to be at least 2+ weeks out and that it would take 3-4 days to get me the boat after they picked it up. I was getting quotes anywhere from $4,000 on up to over $7,000 and doing the math, I figured I could do it myself for less than $2,000. So, I drove out, bought the boat, trailered her back to Seattle and my total expenses were indeed just under $2,000. The journey took 7 days and I got back home early in the evening on day seven. If you have the time, effort and desire, as well as want to go the cheapest route... that's what I'd recommend doing. Sure, you'll spend a little on hotel rooms if you stay in them, but it is the cheapest way of going about doing things, and depending on your schedule it can be one of the quicker methods. There were at least two days where I put in 1,100-1,200 miles of driving each day. And the biggest reason for doing it on my own was because the king salmon season was about 2 weeks away, of which I wanted the boat to be ready for it as well as crabbing. I didn't want to wait until after that as well as pay more to have someone else do it for me, if I could avoid it.
The second and third times, I flew out, looked at the boats, had a surveyor for boat two, bought it and then rented a Ford F-250 from Enterprise rent a truck and trailered her back that way. The rental was a bit more expensive, though I forget exact numbers, and they do charge you both by the mile as well as a one way rental fee in that I picked it up in Maryland and dropped it off in Seattle. You also have to pay for a plane ticket, so depending on how much that costs, it could make it considerably more or not. The benefit of flying out there is that the flight is only around 5-6 hours and you don't waste 3-4 days of driving out there, if that's a concern for you. I caught a red eye flight and got there in the morning around 8-9 am, giving me the entire morning to look over the boat, get the rental truck setup, hook up the trailer to the truck, stop and get a few tools and then start driving. Which is nice because if you get a morning flight and land in the late afternoon or early evening, you waste a day or only get a partial day to start out driving. Which isn't bad, if you want an easy first day. Trek number 2 I figure cost closer for $2,500-$3,000 because of the rental truck, one way truck rental, plane ticket and so forth. Boat number 3 was the same thing but Enterprise wouldn't do a one way pickup truck rental, nor would any of the other rental truck companies. Most companies claimed that they didn't have the inventory to do so because of covid? So, I rented a U-Haul box truck and made the 3,009 mile trek back to Seattle that way. This was the most expensive trip that I did because U-Haul did the same as above where they charge you for the rental, a one way fee as well as the mileage. Between that, lodging, food and everything else... I spent just under $4k doing it that way. Though, I was out in Maryland for several days for the purchase, the sea trial run, the Grady White dealer that I bought the boat from had their shop double and triple check the trailer because they knew I was driving across country, etc. So, it would've been a bit cheaper had I not needed to spend the extra several days there.
All in all, I think the best way is to fly out, rent a truck and drive it back. It's the quickest means of going about doing it, of which I can do a one way trek in 3-3.5 days depending on how fast I'm driving and how far in the day. Most people probably aren't going to want to go balls to the wall like that for the driving, and the last trek I did most days around 700 miles or so in each day. Which is completely doable, especially in the spring/early summer when you've got a solid 8-10+ hours of daylight and you're driving east to west, which you'll go through different time zones and gain time as opposed to losing it. If you have the time and want to save money, driving out and back is a decent option, that being said on day 3, I was getting a little bit antsy and thought to myself... I should've spent a little more money, flown out and saved some time driving. But like I said, if you don't mind the drive and want to see the country or make a roadtrip out of it, it's not a horrible option either. I'd never driven across country before and it was fun to say you've done it once, out and back. I think your biggest considerations will be if there's a rental truck company willing to do a one way truck rental, costs of renting a truck, fuel costs and so forth. Yourself being in the Seattle area know that it's around $4.50 a gallon for gasoline out here, though it's usually always considerably cheaper in the midwest. But, I'd add up your potential expenses, how long you think either way will take and what makes the most sense for you. If you do drive one way or both, in Montana make sure you call ahead or book a reservation beforehand. Apparently there's so much traffic going through Montana that most towns or cities don't have enough hotels/rooms to be able to accommodate everyone going through. So be sure to make a reservation I'd say at least the morning of, if not possibly a day or two in advance. I also tend to avoid the Florida boats, but either way, good luck and if you have any other questions, feel free to message me.