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So you are going to have a few "hallways" connecting the two MHs and then close off the ends? So there will be "dead" space in between them?

Are the trailers already in place? I don't know how to shimmy them together, think when they do double wides they have some super duty sliders they use of some sort. I wonder if a couple heavy duty come alongs would work? Or maybe strategic jacking of one side and then the other. Not sure that would work or how safe it would be.

Just an idea to consider. I'm assuming that the majority of the support, for the 'breezeway' connection is going to be coming from the foundation or at the junction where all the floors are joined. Which is the normal way to build. Foundation is the base and build on top of it.
I think that is where the structural issues will arise.
The trailers aren't of equal weight and the base foundations aren't ever going to be uniformly level either. So the connection between the 2 trailers is the breezeway, and the breezeway will act as a fulcrum. Think of a balance, if the weight isn't equally balanced and supported, the midpoint of the balance will be off center. This will cause the breezeway (the weakest structural point) to shift in order to compensate for any inequalities in the balance between the 2 trailers. When that happens the breezeway (the weakest point) will flex to restore balance, causing it to fail structurally.
The best way to compensate for this is to use a suspension style of construction. The breezeways should receive the majority of support from above and the breezeways should be hanging or suspended between the 2 trailers. Because the breezeway is hanging, it will be more flexible and able to accommodate shifting. I think fortifying the exterior walls and roof joists will allow the load from the breezeway to be supported. Also because the support is coming from above, you can easily level for any flooring irregularities between the 2 trailers.
Just an idea.
Good luck

Any mobile home mover should be able to slide the two up tight to each other, they do it with double wides all the time. It should only take an hour or so.

Greg

Cool project and good luck with whatever you decide.

I'd set them up wherever/however I wanted, and prioritize the footings to make them permanent before I did anything else major between the 2. You can always hold off the remodel expense of a room or 2 if needed. Get them permanent then continue with connecting them if you decide to.