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The problem with the small dolly, is what if you have a flat? The larger trailers are 4 wheel!
Whenever I use a trailer, I rent from Uhaul, a large drive up style, similar to WideSpreadpanic's, but with ratchet tire grabbers.Also for 10 bucks or so both the trailer AND your car on the trailer is insured!!!!! Usually about $150 for a 3 day weekend. Most of us do not have insurance on our new finds when trailering home.
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Well if you tow with a dolly you have four wheels on the ground...if you tow with a trailer you STILL have four wheels on the ground.
If you have a flat, you change it! I do a lot of towing with my dolly and I have two sets of tires that I mount whenever I'm towing any long distances.
I have one set with a 5.5" Ford pattern for '48 and earlier Fords and most Ford pick-ups. And I have one set for Ford and MOPAR 4.50" patterns. Now I'll have another pair with TR wheels because I have to pick-up my TR2 in Tennessee.
My regular insurance collision policy covers my truck and light duty trailers. If you have a collector car that has any value you should have it insured BEFORE you move it...I'd really hate to try to convince U-Haul's insurance company that the "OLD" car you are towing is a classic...it may be but they will pay as if it was just an "old car".