The tail-wheel vertical pin must be vertical to work properly, and this means the swivel has to be run under load with the deck at some designated height off the ground and with the 3 pt. hitch geometry to support this arrangement. THEN a high caster angle relative to the vertical pin should work. Except, this tail-wheel frame has very little lateral stiffness. Get a welder to box in the front & rear of the U-shaped tail wheel frame. Better yet, make a new one using steel twice as thick. That one looks like it could be straightened by hand with a pipe wrench.