shifting and brake problems

For some reason when driving for long periods of time, my shifter doesn't want to go into any gear while stopped. A quick 15-20 minute drive and everything is fine. Only when the car is hot. When I do manage to get it into 1st or 2nd, I don't hear gears grinding except trying to get into reverse. The cables seem to be adjusted correctly, fluid level at full, so I don't know what it could be.

As well, the brakes act weird under the same driving conditions. They don't grab until the pedal is right near the floor. First time it happened I thought I didn't have ANY brakes (freaked me out). Fluid is at full. Any ideas? I hope I explained myself well enough. Thanks.

When was the last time you bled both systems?

I've only bled the rear brakes when I replaced the calipers. I had the front brakes replaced at a shop two years ago, I assume they bled those properly. How do I bleed the clutch? I've never done that before. And what kind of fluid is preferred?