57 Chevy shifting issue

[TwoFiftyShifter]

We've been having an issue with our '57 3100 for ahile now. It's a 235 with a 3 on the tree, and it doesn't shift correctly. 2-3 works great, but the 1st-R gate is difficult to get into, takes two hands to pull it up into 1st/Reverse. It's odd, some days it works pretty well, some days it forces me to just put it in 2nd and slip the clutch at a stop light. What could be the problem?

Also, the brake lights have stopped working out of the blue, bulbs are fine becuase the tail lights work..... Where should I troubleshoot the break lights? At the pedal?