robow7 that is always going to be a problem you run into with the 2p 50/50. Your problem is the outside main ties off at 8H which gives you four blocked holed at the top of the racket (7h $ 9h.) assuming you have enough string you could pre weave the top 9 crosses with a loop large enough at the 9th cross to pull tension and a tail just long enough to stick out 7h. Finish your mains and start you crosses with no blocked holes at top.
There are a lot of other methods but for me cutting an angle on the string and using paraffin wax for lube seems to work good. I look at the side of the racket for the largest gap between the string and frame and try to turn the string so the point is on that side. Pushing short section with bend nose pliers works for me. Try not to cut too long of a point as it weakens the string and when the point gets flimsy cut a new one. Try getting a scrap piece of string and see if applying a little heat will help to stiffen the string. You may try a drop of superglue on the tip then wipe it off to let it dry. Acetone tackles the glue off your finger.
I have the ability to drive people crazy, not sure if I was born with it or I learned it but I'm damn good at it.