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It may be fine. Or not. Clutch loss is high on my list of potential problems in the given scenario. I'm not saying it'll happen. I'm saying that if something bad happens, clutch loss is a top candidate. Is this an auction trailer? If so, brakes and tires are always suspect. You'd probably get...

Clearance on the hitch - Ideally you'd want to be able to turn the towing vehicle 90* to the semi trailer and not make contact. I'm not certain because I can't find dimensions, but I don't think 18" gives you that. In the real world, in a one time retrieval trip, as long as the actual angle...

Repair/rebuild of a purpose built converter dolly is probably less work with a better outcome than fabbing one out of a 105. I see no reason you couldn't use military 5ton wheels on it. Do you already have the wheels and tires? What's currently on it? On the topic of the brackets, as long as...

I share your concerns about the distance from the end of your truck frame to the landing gear on the trailer. That might be close enough to make contact in a really tight turn, or especially when backing. I'll go look at some diagrams and comment further. But backing a converter dolly is...

Since you'll be mounting the 5th wheel plate either way, I'd mount it to the deuce and remove several possible points of failure. Last spring I moved a similar semi trailer on a converter dolly from KS to IL to NM behind my M925. I don't know that an M105 is up to being a converter dolly. I...