360 Oil Dip Stick Tube Angle/Placement Into Block

The tube has the lower end crimped outward into a ring shape about 1/2" above the lower end; the tube is just pushed into a hole in the block and this expanded area stops it from being pushed in too far.

The tube tend to bend at this expanded area and can get weak. You ought to carefully examine the expanded end of the tube where it goes into the block with a mirror and flashlight to see if it is starting to crack and break at that point; that could explain why the dipstick was hard to remove and replace and why rotating it made the insertion of the dipstick easier: the tube may be cracking and twisting and the dipstick was hitting part of it.

If the end of the dipstick was straight and not mangled, then it is likely a problem in the tube. But make sure that the end of the dipstick is straight. If it is bent so that it bends towards the crankshaft, then I'd straighten it out. Someone showed a pix here within the last year of a dipstick that got snagged in the crank!