727 small block shifting issues

never done it but i'm sure a youtube video can walk me through it.

Tell ya something about that trans.
If second gear isn’t available for some mechanical reason it will skip right to third.
The fact that yours stays in first usually means a sticking valve in the valve body or governor.

While running in first what does it do when you let off the throttle?
Does it have engine braking, or just act like it’s in neutral?