Re: Help me find my next boat 24-29 foot
I advise you to really mull over your stated preference for an inboard diesel. What is it about that design that appeals to you?
I say this because there are sailboats with an outboard hanging off the stern, which I'd agree is not very desirable (aesthetically or performance-wise when motoring in rough conditions). But there are many 25-28 footers though with purpose-built outboard wells that are a very different story. Easy access, modest maintenance, decent performance and lower cost of ownership are all there. This design could be in a boat you otherwise find to be a very good fit for your other needs.
Our Hinterhoeller HR28 has such a design and since we use the engine maybe only 10% of our time in the boat, we find our outboard-well design to be entirely satisfactory, even preferable. When our 15 HP needed service, out it came and we dropped in a 5 HP a friend had... 30 minutes and we were back in business. (We were also shocked at how well 5 HP moved a 7,000 pound boat, though in calm conditions).
Anyway, I encourgae you to consider if a purpose-designed outboard well could meet your needs in a 25-30 footer.