Into Gear problems
 

On my 99 F-150 Im having issues when trying to take the truck out of park into the drive position, There seems to be a problem with the safety interlock, I apply and pump the brake pedal and then have to wiggle and wrestle the shift lever quite a bit to get it to go into Drive from park, Any tips or suggestions ?

shift problems
 

I have the same problem with a 98. I don't know what causes it, maybe just wear. I found that if I moved it back and forward gently, I could feel when it was positioned correctly to shift.
There is probably some on here who can give you a better answer if they will respond.
Good Luck

Yeah, something definitely worn, what to replace to fix it ?

I don't know what is worn. What I would do to find out is remove the steering column(it isn't difficult)and disassemble it. But that's just me.
Alternately. I would get another column and swap them out.