I see your point but only to a point. My boat is an 02 so it's not in the new boat price discussion. If it were in my family's budget to own a new boat I would thought but again that only to a point. I know I'm sounding vague. I'll try to make sense.
I'm a machinist that drives 60 miles a day and park in a gravel parking lot at work or a gravel driveway at home. I drive a $2500 car. I've had nice cars but really all I do is fret over it smelling like a machine shop or trying to keep it clean inside and out etc. Plus putting miles on it too. A cheapo car that's reliable is all I need. My wife's trailblazer pulls my boat pretty darn good so it's the tow rig. Now would I feel right about buying a new boat knowing the trailblazer is getting long in the tooth? Nah not really. But if I had a newer lower miles truck or suv and could afford both I sure would. It wouldn't bother me to tow a $30k plus rig with a $15k truck. I'm sure lots of people think I'm stupid for driving a $2500 car to work while owning a $12-15000 bassboat too. Maybe I am. Maybe my priorities are a little lopsided but the time I get to trap my boys in that boat with me makes it worth it. I'm not saying you or anyone here thinks that way, I was just saying.
It just depends on budget and what your uses of the vehicles are. Like I said my old car just has to go from here to there. That's just my situation though.
Now if I worked closer to home I'd sell the old car and buy a couple 12' talons for the boat and sell the 8 footer. Now that's getting priorities jacked up lol.