I've done what your asking more than once and NO I would not do it again.

Towed a trailer with my 73 340 4speed and my 70 convertible on it and no engine. Had a flat towing the empty trailer from TN to LA because the tire rubbed the wheelwell under the load.
Coming back with my vert on it it went OK cause the balance was better and less load on the tounge.
Went back for my 73 Charger. Made it back and noticed that the rear bumper was bent from the load. This is the 73 bumpers with the steel reinforcements that can take some serious beating and not the 71 and older thin chrome veneers they call bumpers.

Went back to get my 74 RR/GTX & my 70 Barracuda. Used a tow bar on the Cuda behind the GTX. That Cuda wanted to drive half the trip. Had to leave the interstate and go on backroads that weren't rutted out. White knuckle driving all the way.

Lastly I tried to bring home my son's Buick behind my Satellite on a dolly. I was only going 6 blocks or so and still nearly trashed my car. Going slow (~15 MPH) I hit the brakes and slid into and intersection where it Jack-knifed in the middle of it.

Last time out I had a LWB 1/2 ton truck and a trailer for my Satellite Parts car. Smooth, Easy and no problems.

It can be done but it is stupid to try it. I know, I was lucky.