While motoring my 1977 Hunter 27 from my Summer dock site to my Winter hauling and storage site, the old Yanmar YNB-8 pretty much died on me. No power, lots of brown and then white smoke, etc. My mechanic and I did some preliminary work such as changing fuel filters but it ultimately looks like a damaged rings or worse. We will do a compression check after Thanksgiving but it doesn't look good for the old girl. So my thought process is centered upon whether to repair/rebuild the diesel or replace it with an outboard.A little background on the boat and it's usage:The boat was poorly maintained before I bought it in October 2005. (I bought it as a project - and I have not been disapointed...) The engine was never rebuilt or repowered as far as I know but did run fine all summer. There are some soft spots on the deck above the cabin. I have rewired it (AC and DC) and added new cushions, stripped and sealed below the waterline, painted topsides, replaced the cutlass bearing. New sails will be added this winter. I plan to continue working on it until it is comfortable and looks nice. I expect to keep it for about 10 years. I use it primarily for daysailing and coastal cruising.On the plus side for rebuilding the diesel I come up with:Keeps the boat as designed.Handling underpower will be about the same. (The devil you know)No shaft openings to fill.On the plus side for removing the diesel and adding a new 18HP 4-stroke outboard:Less expensive. (~$4K to rebuild vs. ~$3K for outboard, controls, brackets, installation.)I can take it with me if I decide to change boats.Handling underpower may be improved. (Less prop walk to port in reverse?)Everything (engine-wise) will be new.More power - the 8HP diesel was almost under powered.Quieter - certainly in the cabin.More storage space in the cabin.So finally my questions:1. Has anyone had experience doing this? If so, what were the gotchas, pluses, and minuses?2. Will the handling be much different?3. Is there a brand of outboard that is better or one to avoid?4. Any other suggestions?