Don: It seems to me that opinions about brands of outboards are like opinions about makes of cars: everyone has their own pet peeves and preferences. Someone may hate Chevys, but that doesn't mean you will too. Pick an outboard based on the features offered, and your comfort level with your dealer or servicer.
After sailing my Oday 23 for 11 years with two different outboards, I offer these suggestions:
If you are replacing a two stroke with a four stroke, you will have to upgrade the bracket too. Brackets rated to accomodate four strokes (not just the extra weight, but the extra torque as well) will be too wide to fit on the supporting transom wedge. Your local stainless fabricator should be able to make you a plate that can be bolted to the wedge that will accomodate the new bracket. Or, you can build a new wedge.
You should buy the longest shaft available. The prop on my 20" long shaft cavitates when I make a very sharp turn, or in any kind of seaway. Longer is better. At least a couple of manufacturers offer 25" models. I would look into those.
Electric start is a beautiful thing. I love the convenience, but my wife thinks it is a safety necessity. In an emergency, I don't know if she could use the pull start; she is fine with the electric start.
Good luck, and happy hunting.