Alright guys I just bought a 87 f150 with the 351w and a c6 transmission. The transmission shifts seems to shift really late and hard into 2nd gear. Could this be a vacuum issue and if it is where should I start?

 

Check for vacuum leaks - you should probably idle around 15 psi. You should have a vacuum shift modulator on the right hand side of the trans - check for vacuum there. Also that modulator could be bad. If replacing it get an adjustable one.
You also have to make sure your kickdown linkage is adjusted properly.
After that I'd be looking at a dirty governor