Yikes that's a lot of money to keep dumping into something...my situation is a little different but once my last truck was going to need something more than my payment, it was gone. Those amounts in the thousands I would be running away from it, unless you have some warranty that will cover those things obviously. Even so, major and expensive repairs like that would be pushing me into getting rid of it.
In terms of buying out of state, it's what I have done with nearly every truck I've bought. Being in NY, it's better to drive down to Maryland or Virginia for vehicles cause up here you will see rust somewhere after one winter. I also search for very specific and hard to find trucks, so I don't go out seeking a good dealer, just the right truck. In terms of the cheaper east coast trucks, just be mindful of where they have been used and do your homework on the truck and it's history (carfax/buildsheet etc). Obviously I'd recommend staying away from trucks used or registered in the Northeast, stuff starting in Maryland and further south should be in better shape. If you don't already have it, here's a link to the build sheet website. Just need to delete the vin # out of the address and copy/paste the new vin# of a truck you're looking at online in, and it will give you the buildsheet and every option the truck was built with.
https://www.dodge.com/webselfservice/BuildSheetServlet?vin=1C6RR7PT9HS746749
I'd also look thoroughly through the carfax history for maintenance/recalls done, and check everywhere the vehicle has been registered by the owner. Also, if you're looking at newer trucks that still have factory warranty remaining, look for trucks that are from Canada. A ton of them make their way over the border and generally don't have their remaining warranties honored. You can find that info on the build sheet, towards the end of the standard equipment I believe, right before the optional equipment list starts. Also, on the carfax it would show that it was registered at some point by the original owner in Canada.
Great point, definitely forgot about that aspect of selling privately as well.
Not to mention, getting a sale timed up with the time you trade in is difficult. Unless you don't need those funds for a down payment, but otherwise you'd have to sell it first and then find your new truck. In our state with the sales tax trade in credit, I paid taxes on around 14k rather than 36k (cost of truck) due to getting 22k for my trade in. That's somewhere around a $1700-1800 difference with our sales tax, and factor in that I got close to private party value on the trade anyways, so I traded.
Also, I didn't have to worry about the timing working out well, and that dealer took a truck with problems off my hands that I didn't feel bad about or have to fix after the fact. Given the OP's, situation, I'd feel better about dumping it off on a dealer anyway.