Yes. The experence of a coastal sailer, but not deep blue water. I have been pushed aground off Tarpon Springs, Fla. in a 35' Vangard. I have tried threading the 1000 islands of south Florida in puffy days when everything seemed to go wrong, and beat my way in Tampa bay against tide and wind for hours. Trade it, hell no! But I also recognize that it could have got dicey and I could have lost my boat, crew, and put other people in danger for my stubborn stupidy.
One of the gains in growing older is to realize that you are only a frail human and you are not superman and there many people who care and belive it's their duty to come to your rescue when you do something that endangers you and yours. I now try not to be one of those who needs their aid.
I am not a fan of outboards on boats as large as your Alberg. Why hang the engine out in the weather off the stern? If you tip it up, you have to put it down to use it. If you leave it down you're dragging a prop through the water(isn't this why you wanted to get rid of the inboard) Ever try to tip down an outboard in a choppy sea? If you unship it to store it below, (space, smell) you have to hang it back to use it. This can be fun at sea(please don't drop it, engines hate total emerson) assuming you tided it off.
On the other hand you inboard is big, heavy(think balast) but inside. You can work on it even at night, rain. It will get you a whale of a lot further on an equal amount of fuel.(think becalmed 20 miles out) and a two blade prop lined up with the keel really isn't a noticable drag unless you are racing. You can line this up with a crayon mark on the shaft when the blades are in the correct position, if you're that worried about it. It can charge your batteries, heat your cabin, and can, in an emergency, pumb your bilge.
Yes, they REQUIRE mantainence, space parts, oil changes, filters; but guess what so do outboards. Your Yamar with care and attention will out live your boat, will the outboard?
This is my opinion. Opinions are as the drops of water in the sea, all sailors have them.
"it's the trip, not the destination"