[Faster]

The Cal T-2 is indeed a PHRF sleeper that does very well on the race course when well sailed.

However as a 35 year old boat of limited market value, despite it's servicability, it would be difficult to justify the cost of repowering with a new diesel - and certainly you could not expect to recoup that cost in any significant way through resale. If you're prepared to take a chance on a used engine at a good price, that may make more sense.

Repowering as you suggest could involve any or all of the following:

Modifying the engine beds (spacing and angles may not match)

Different shaft/strut/prop/coupling etc.

Modifications to the fuel tank and fuel system

And on it goes. 20+ years ago we replaced an Atomic 2 gas engine with a Volvo 2001 series diesel in a then-ten-year-old Ranger 28 - we were able to reuse the shaft but had to seriously modify the beds and fuel system - and as an entirely DIY project it still cost about $4500 1984 dollars - engine and bits only, no labour charges.

So really, unless you're having a great deal of trouble keeping the prop in the water now you might want to reconsider.

I agree the boat would look a lot better without the outboard on the transom, though!