Great post and many intriguing thoughts, end of the day, either option is the correct answer. How you plan on using your boat and why you are buying it should be the driving force behind your decision. With a side question on the bad fuel part, it doesn't matter how many engines you have, if the fuel is bad, all engines can be lost, including get me homes (unless hydraulic).
My thought process comes in the form of Cost, and not just money. Everything comes at a cost. Cost can be the peace of mind, money, or risk.
Personally, I have a hard time with single engines and a wing get me home engine. You mean to tell me you want me to rely on a small engine that gets turned on once in a while with a prop and a shaft that has been in the water with lack of use, and you want me to rely on that option to get me out of a bad spot? I am not comfortable with that. Especially most wing engines give you what 3 knots? Will that be enough to get you through an inlet or turn you around in a bad storm? Plus, you still have an elevated upkeep cost for the cost of keeping the wing engine in great condition, again even if you do turn it on or conduct maintenance. Cost is peace of mind and Risk.
If I go single engine, I will go with a hydraulic same shaft get me home that runs from my gen set, and depending on my Genset I can get 5 to 6 knots. Again, unless I lose my prop then there is that. Again...Cost is a risk.
A single-engine is a lower operating cost, not only less fuel but less upkeep and maintenance. That is a pretty good blinder for all of us, cause at the end of the day we think about cruising and relaxing on our boats, so we want to fund that rather than fund something that might happen once or twice during the lifetime of our boating experience. Cost is Risk
The multi-engine option comes with added cost, but better peace of mind. The operating budget is the balance, yes the multi-engine is worth the cost, but is the cost going to keep you from cruising and enjoying the boat? Cost is Money and peace of mind (positive and negative mindset).
For me, I would rather go for the multi-engine, added maneuverability, and added peace of mind when I do my Bahamas run or farther.
It is in the same category as Radar, no one wants a radar unless you get caught in fog or are forced to move at night without it. The same thing with the multi-engine, no one wants the second engine until you want to cross a large barrier of water with no sight of land.
If you want to go the distance you want the second engine to take you the distance. Plus, if your heart desires to take you somewhere but your thought process is your single engine, then a multi helps you with your travel destination list, again Balancing, cost and risk.
What is it worth to you?