2000/F350/7.3L/4X4/Auto
My oil dip stick has always been tough to get back in taking way more effort than it should but recently it takes me getting under the hood and feeding it in with two hands at an inch at a time...and at 3' long checking the oil has turned into as seldom as possible.

 

The only thing I can think of here is that your stick or tube has gotten bent.

 

Sounds to me like the tube is either bent or clogged. I would recommend that you take it off (only have to remove 1 nut). Visually inspect the tube. If it is not kinked, use some brake cleaner to clean it out. It might take running the dipstick in and out with the brake cleaner in it several times to get it clean. Be sure to get a new o-ring for the bottom, because the old one will never seal again.

 

When removing the nut that holds the dipstick in place, be sure to put a "backer wrench" behind it to prevent the entire bolt from turning and bending the dipstick even further.

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