3208's @ 375HP

No reason to worry.
The factory self destruction timing on those engines is set at 6000 hours, so obviously someone already hacked it, and you can now safely run them forever.

Yeah, sorry for the previous joke, I just couldn't resist following up your idea of self-desrtucting engines.

Back to the point, I'm far from being a 3208 expert, but also my understanding is that they are very durable engines.
Possibly aside from the higher power version (440hp, if I'm not mistaken).
But someone with a more specific experience will soon confirm or correct, as appropriate.

There is nothing positive about high strung 3208s.
Non replaceable liners. High HP blocks are different from the original design.
High HP core blocks are getting harder to find.
And yet, some folks here have had good luck. Back to that divine blessings.

I have witnessed just to many horror stories.

There could be a reason that you keep asking about old & over HP - hour engines.
Are you looking for another dock queen?
I remember in another post you wanted to cruise to FL.
There is no savings in picking up old abused engines.
Unless your going to rebuild or repower.

With a rebuild or repower attitude, find a solid boat that fits what you want.

I remember Fleming's with the high strung 3208s in them. Decent boat, insane engine selection.
There was no redeeming values below her decks.

If you don't mind, I'd like to type a lil more;

I have a dream;
Some way, some how, some body builds a serviceable boat with correctly match power.
The Hatt 58 LRC can fit that tab.
I was on a Deerfoot 64, that exemplified a properly built boat for a long life.
I am told others are out there that compare, my view from this swamp does not reach far these days.

IMO; A boat of any quality should be used and maintained well.
Anything mechanical needs service and will need access. Blowers to windlasses.
The main engines should be in long life HP tune.
The main engines should be in a real and proper sized engine room.
During her extended life, engine work will be done including overhaul.
The main engines should be rebuildable. This includes replaceable liners and room to work.

What is the year and HP rating of the 3208's you're looking at? The 3208 is a good motor until you try to squeeze too much out of it. Up to 325hp is pretty safe, some will say the 375 hp is OK but absolute top. I think 375 is pushing it but depending on maintenance and how they were ran maybe not a deal breaker if you love everything else about the boat. If they are 400+ hp I personally wouldn't touch them.

I got a laugh out of your comment that with a $300k budget you can get turn key that needs nothing. There is no such thing at virtually any budget. Boats always need something. Even if its perfect today something will happen tomorrow. That's just the nature of the beast.

Duh - you listed the HP right in your title. Sorry, my bad, I know I saw it somewhere.

Amen to that.
And just in case someone might raise the objection, nope, not even brand new boats "need nothing".
A boat that needs nothing is the perfect definition of what wishful thinking is all about!

Just found a 2000 cut sheet on a 450HP Cat 3208 TA. Listed for one year.
Shortly before and after a 435HP was offered.
The madness.
These were disposable engines in fancy and short sport fishing boats.
These were not rebuilt but replaced. Hence large saloon doors.
Modern outboard rationale.

Replacing was the preferred method for the performance minded.
Call your local Cat distributor. Ask what support is still available. Have your Depends ready.

You don't want these grenades below decks of a plush yacht.

Now, in natural tune, the 155 or even the 3208 T in 260 HP, could run and run and run.
But, the rebuild day is coming. It's not rebuildable on board.

If you needed twin 375 HP engines in a trawler, this may have been a cheap and short viewed answer.
I'll never understand the need to try and over power a trawler to begin with.
I've got to stop pounding this. Sorry to keep throwing negative waves at ya.

Lets find you kids a nice boat.
We have not got any styles from you yet?
You need speed? Cockpit? Head room? More that 1,2 or 3 cabin & heads?
Fly bridge? Sun pad?
Hello pad?

I don't have anything real bad to say about Bayliner or Meridian boats.
They are solid and have a good engine package. Mostly cummins and I feel properly powered.
Not a lot of displacement, nor a lot of V.
Having lived on the Huckins dock for over 10 years and studying this similar hull design, it is a good (not great) compromise.
You will still have to pick the weather days but they don't twist apart.
They had built on Friday issues as most cost/point boats have. Survey them well.

For good service with common service parts.
Just watch for sharp edges as I have spilled much blood in these.

You didn't mention the Great Loop before (or I didn't notice).
One of these puppies can work well.