Is it possible to have too much rake? Some of the old timers that I sail with keep telling me that I've got too much.

I've raked the rudders under and have little weather helm, and get my 6:1 within 2 inches of block to block with the main I bought brand new last season and have only sailed perhaps a dozen times.

I seem to be able to point much higher, however they seem to have a little more boat speed when falling off, well more than I do when I fall off.

Depends on the wind speed. In high winds (over 20 plus) I have seen two blocked mains with floppy leechs smoke. They had loosened the Jib halyard and let the mast lean WAY aft. It was a matter of survival for light crews at a high wind Worlds event.

Higher the wind... rake more aft. You do give up a little down wind though. You have to adhust for the conditions and your sailing skill set.

It is good to get to the weather mark first! Pointing higher helps.