how I hate these decisions
 

The tow vehicle is on the last leg, it's thousand dollaring me to death. So I'm checking prices and even a recent used truck with the tow capability ( 2500/3/4 ton) I need probably exceeds the value of the boat. I don't need a truck for anything else so it's hard to justify the expense. Very well may be time to move on to a smaller boat and tow vehicle or just get out of this game.

Have you thought about going older? Nice thing about trucks, is people collect them like cars. You can find mint older trucks with big engines cheap. My friend just wanted to tow 5miles from his house to launch ramp. 20ft Graddy White. found a 1970 F100 with a 390 in it show truck for $6k.

What budget are you trying to stay in?

How far do you need to tow?

And what are you towing?

I know that feeling. My truck is a 2004 and only has 40K miles on it. As long as i still own a boat, I'll probably never get rid of it just because of the price of new trucks.

The truck that I currently have is a 2001 Dodge 2500 v-10, 140k miles and lots of stuff dying. Latest is frequent brake line failure due to corrosion.

I'm towing close to 11 thousand pounds total.

If it were me...

I'd look into buying a Texas or purely southern truck like a 150,000+ mile Dodge; and adding that to your fleet. Then you can move parts from the older truck to the Texas sourced truck as needed, until the Michigan truck is totally defunct. You could be in a truck like above for $15-20K.

. I would keep her alive. I have had those days where all my machines talk to each other and break every other week. Getting a used one you could start the feeding all over.

Look into a southern lived 7.3L truck.

My 2001 Excursion pulls my heavy whore with ass and have been pretty painless other than basic upkeep really with 230k on her.

In my opinion I would look at how much you have into it. If it's a good bit as of recent then you have done most of the work already. If you still have some brake lines that haven't been replaced get them done all at once with the copper nickel lines that don't rust. Also it's easy to bend and flare so you could do it yourself if your handy. Then take the bed off and replace all the fuel lines and tank/s.
When I bought my 05 Chevy I knew it was gonna need all that. I spent 3,000 and know I won't have any lines rotting out in the next 5 years. Then I took the bed off and cleaned the frame with a needle gun. After that slop very liberally some rusty metal primer. Cover that with black and your good for a while. Once your so far down the repair road it's time to just keep going.