car dollies are no better than flat towing, IMO.
and, I see longer than stock front shackles....
your caster is not enuf with the lift and shackles. You need 2.5 degree shims installed between the spring pack and the axle perch, orientate them so the pinion on the pumpkin is lowered. This will increase your caster and help immensely. 2" overstock shackles should only need 2.5 degrees, find steel ones, not alum, and you may need longer spring center pins too to keep things aligned.
Tire pressure...maximum sidewall rating, least rolling resistance.
I towbarred for 2 years behind a 95 Toy pickup, even in snow. Very unsafe, but made me a unwilling expert in the tricks of the towbar.