Personally, if you are going to mess around with the architecture sufficiently to force a compiler modification, you might as well recompile to something else entirely. ARM or MIPs spring to mind.
I agree. The only reason for adding extra instructions is so you can put something on your CV and to have something to talk about over a beer.
In the case of the FPU, the only way it's faster is to make it less accurate. If accuracy is not important then it's possible to make all FPU operations take no time at all, just make them all return 0. It would be just as useful for running all your old FPU apps.
I don't have any doubts over technical prowess but in terms of direction he needs to know that diverging from the original specifications is not what anyone really wants. You can probably find some people that say they are happy with it, but they are probably making assumptions over what they will receive that nobody is even attempting to achieve.
100% 68060 compatible CPU+FPU+MMU is the only "compromise" that I'm happy with, Motorola took things out and people have spent decades making sure the software runs. We shouldn't have to start that process again just yet.
Even if you attempt to make something 100% compatible you will fail, if you start out aiming lower than 100% then when you fail it gets real ugly.